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Synthesis 2017; 49(20): 4535-4561
DOI: 10.1055/s-0036-1589512
DOI: 10.1055/s-0036-1589512
review
Recent Advances for the C–C and C–N Bond Formation in the Synthesis of 1-Phenethyl-tetrahydroisoquinoline, Aporphine, Homoaporphine, and β-Carboline Alkaloids
We thank the Colombian Institute for Science and Research (COLCIENCIAS) under the project No. RC-0346-2013. CEPG acknowledges the fellowship given by the doctoral program COLCIENCIAS-Conv. 617.Weitere Informationen
Publikationsverlauf
Received: 13. März 2017
Accepted after revision: 09. Mai 2017
Publikationsdatum:
21. September 2017 (online)
Abstract
Among the existing methods for the synthesis of bioactive and/or complex small molecules, organic transformations such as C–C and C–N bond formation have been significantly developed and exploited for the synthesis of diverse synthetic and natural fused aza-polycycles. The abundance and biological and physical activities of 1-phenethyl-tetrahydroisoquinolines, aporphines, homoaporphines, and β-carbolines have inspired many organic chemists to seek sustainable and efficient protocols for their preparation. However, these methodologies involve multiple steps and in most cases the key reaction step is based on the formation of new C–C and/or C–N bonds, and this is usually the critical step that lowers the yields and selectivity. This review is focused on the advances made in recent years regarding the synthesis of these selected natural fused aza-polycycles, overviewing the substrate scope, limitations, regioselectivity, and chemoselectivity, as well as related control strategies of these reactions, concentrating on developments from 2010 to 2016.
1 Introduction
2 1-Phenethyl-tetrahydroisoquinolines; Dysoxylum Alkaloids
3 Aporphines, Homoaporphines, and Semisynthetic Derivatives
4 Harmala and Eudistomin Alkaloids and Their Biological Properties
5 Metal-Catalyzed C–C Bond Formation
6 Pd-Catalyzed C–C and C–N Bond Formation
7 Metal-Catalyzed C–N Bond Formation
8 [4+2] Cycloaddition in the Synthesis Of Aporphines
9 Tandem C–N/C–C Bond Formation: The Pictet–Spengler Reaction
10 Miscellaneous Methods
11 Conclusions
-
References
- 1a Chrzanowska M. Grajewska A. Rozwadowska MD. Chem. Rev. 2016; 116: 12369
- 1b Liu W. Liu S. Jin R. Guo H. Zhao J. Org. Chem. Front. 2015; 2: 288
- 1c Chrzanowska M. Rozwadowska MD. Chem. Rev. 2004; 104: 3341
- 2a Laine AE. Lood C. Koskinen AM. Molecules 2014; 19: 1544
- 2b Love BE. Org. Prep. Proced. Int. 1996; 28: 1
- 3a Rakshit JN. Analyst (Cambridge, U. K.) 1921; 46: 481b
- 3b Ramanathan VS. Chandra P. Bull. Narc. 1981; 33: 55
- 3c Bulduk I. Taktak F. J. Chem. 2013; 493870
- 3d Sorianoa MP. C. Shankaraiaha N. Silva Santosa L. Tetrahedron Lett. 2010; 51: 1770
- 3e Abdalla MO. Aneja R. Dean D. Rangari V. Russell A. Jaynes J. Yates C. Turner T. J. Magn. Magn. Mater. 2010; 322: 190
- 3f Debono AJ. Mistry SJ. Xie J. Muthiah D. Phillips J. Ventura S. Callaghan R. Pouton CW. Capuano B. Scammells PJ. ChemMedChem 2014; 9: 399
- 3g Ye K. Ke Y. Keshava N. Shanks J. Kapp JA. Tekmal RR. Petros J. Joshi HC. Proc. Natl. Acad. Sci. U.S.A. 1998; 95: 1601
- 3h Chougule MB. Patel AR. Jackson T. Singh M. PLoS One 2011; 6: e17733
- 3i Rida PC. G. LiVecche D. Ogden A. Zhou J. Aneja R. Med. Res. Rev. 2015; 35: 1072
- 3j Singh H. Singh P. Kumari K. Chandra A. Dass SK. Chandra R. Curr. Drug Metab. 2013; 14: 351
- 3k Mahmoudian M. Rahimi-Moghaddam P. Recent Pat. Anti-Cancer Drug Discovery 2009; 4: 92
- 3l Mahmoudian M. Curr. Top. Pharmacol. 2006; 10: 81
- 4a Babua RA. Reddya NS. S. Reddyb BJ. M. Reddy BV. A. Synthesis 2014; 46: 2794
- 4b Trinadhachari GN. Kamat AG. Balaji BV. Prabahar KJ. Naidu KM. Babu KR. Sanasi PD. Org. Process Res. Dev. 2014; 18: 934
- 4c Kelleher CJ. Cardozo L. Chapple CR. Haab F. Ridder AM. BJU Int. 2005; 95: 81
- 4d Chen Y.-C. Chen C.-Y. Kuo H.-C. Urol. Sci. 2010; 21: 38
- 4e Han JY. Lee KS. Park WH. Park CH. Lee JG. Lee JZ. Kim DY. Na YG. Kwon DD. Choo MS. PLoS One 2014; 9: e112063
- 4f Chapple CR. Cardozo L. Steers WD. Govier FE. Int. J. Clin. Pract. 2006; 60: 959
- 4g Kosilov KV. Loparev SA. Ivanovskaya MA. Kosilova LV. Arab J. Urol. 2015; 13: 203
- 4h Pelman RS. Capo Jr JP. Forero-Schwanhaeuser S. Postgrad. Med. 2008; 120: 8
- 4i Basra R. Kelleher C. Ther. Clin. Risk Manage. 2008; 4: 117
- 5a Fañanás-Mastral M. Teichert JF. Fernández-Salas JA. Heijnen D. Feringa BL. Org. Biomol. Chem. 2013; 11: 4521
- 5b Reddy NS. S. Reddy BV. S. Tetrahedron Lett. 2014; 55: 3157
- 5c Verzijl GK. M. de Vries AH. M. de Vries JG. Kapitan P. Dax T. Helms M. Nazir Z. Skranc W. Imboden C. Stichler J. Ward RA. Abele S. Lefort L. Org. Process Res. Dev. 2013; 17: 1531
- 5d Owen RT. Castañer R. Bolós J. Estivill C. Drugs Future 2009; 34: 5
- 5e Hoch M. Hoever P. Zisowsky J. Priestley A. Fleet D. Dingemanse J. Pharmacology 2012; 89: 53
- 5f Mang GM. Dürst T. Bürki H. Imobersteg S. Abramowski D. Schuepbach E. Hoyer D. Fendt M. Gee CE. Sleep 2012; 35: 1625
- 5g Srinivasan S. Simms JA. Nielsen CK. Lieske SP. Bito-Onon JJ. Yi H. Hopf FW. Bonci A. Bartlett SE. PLoS One 2012; 7: e44726
- 5h Dingemanse J. Gehin M. Cruz HG. Hoever P. Drug Des., Dev. Ther. 2014; 8: 397
- 5i Neubauer DN. Curr. Opin. Invest. Drugs (BioMed Cent.) 2010; 11: 101
- 6a Jaeger RJ. Lamshöft M. Gottfried S. Spiteller M. Spiteller P. J. Nat. Prod. 2013; 76: 127
- 6b Naveen B. Mudiraj A. Khamushavalli G. Babu PP. Nagarajan R. Eur. J. Med. Chem. 2016; 113: 167
- 7a Sun B. Morikawa T. Matsuda H. Tewtrakul SM. Wu LJ. Harima S. Yoshikawa M. J. Nat. Prod. 2004; 67: 1464
- 7b Cao L.-H. Zhang W. Luo J.-G. Kong L.-Y. Helv. Chim. Acta 2012; 95: 1018
- 7c Shi XX. He D. Li SB. Lei X. Yang H. Asian J. Chem. 2013; 25: 6387
- 7d Zhang Q. Dong J. Shi X.-X. Lu X. Eur. J. Org. Chem. 2012; 3317
- 7e Omura K. Choshi T. Watanabe S. Satoh Y. Nobuhiro J. Hibino S. Chem. Pharm. Bull. 2008; 56: 237
- 8a Kartal M. Altun ML. Kurucu S. J. Pharm. Biomed. Anal. 2003; 31: 263
- 8b Pandey RK. Shukla SS. Tiwari R. Chauhan NS. Spatula DD 2016; 64: 103 http://www.spatuladd.com/
- 8c Monsef-Esfahani HR. Faramarzi MA. Venus M. Rouini M.-R. J. Appl. Sci. 2008; 8: 1761
- 8d Wang X. Geng Y. Wang D. Shi X. Liu J. J. Sep. Sci. 2008; 31: 3543
- 8e Akabori S. Saito K. Ber. Dtsch. Chem. Ges. B 1930; 63: 2245
- 8f Kusurkar RS. Goswami SK. Tetrahedron 2004; 60: 5315
- 8g Spenser ID. Can. J. Chem. 1959; 37: 1851
- 8h Pakhare DS. Kusurkar RS. Tetrahedron Lett. 2015; 56: 6012
- 8i Cao R. Peng W. Wang Z. Xu A. Curr. Med. Chem. 2007; 14: 479
- 8j Moshiri M. Etemad L. Javidi S. Alizadeh A. Avicenna J. Phytomed. 2013; 3: 288
- 8k de Meester C. Mutat. Res. 1995; 339: 139
- 8l Pfau W. Skog K. J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 2004; 802: 115
- 8m Abe A. Yamada H. Anticancer Drugs 2009; 20: 373
- 8n Zhao T. He Y.-Q. Wang J. Ding D.-M. Wang C.-H. Wang Z.-T. Phytother. Res. 2011; 25: 1671
- 8o Moloudizargari M. Mikaili P. Aghajanshakeri S. Asghari MH. Shayegh J. Pharmacogn. Rev. 2013; 7: 199
- 8p Vachnadze V. Suladze T. Vachnadze N. Kintsurashvili L. Novikova J. Georgian Med. News 2015; 243: 79
- 9a Kaul PN. Brochmann-Hanssen E. Leong WayE. J. Pharm. Sci. 1961; 50: 840
- 9b Essink AW. Lohuis CP. Klein Elhorst JT. Rutten WJ. J. Chromatogr. 1991; 570: 419
- 9c Davis PJ. Seyhan S. J. Pharm. Sci. 1980; 69: 1056
- 9d Neumeyer JL. Neustadt BR. Weinhardt KK. J. Pharm. Sci. 1970; 59: 1850
- 9e Neumeyer JL. Neustadt BR. Oh KH. Weinhardt KK. Boyce CB. Rosenberg FJ. Teiger DG. J. Med. Chem. 1973; 16: 1223
- 9f Deleu D. Hanssens Y. Northway MG. Drugs Aging 2004; 21: 687
- 9g Gunzler SA. Expert Opin. Pharmacother. 2009; 10: 1027
- 9h Munro AD. Psychopharmacology (Heidelberg, Ger.). 1986; 88: 124
- 9i Picada JN. Roesler R. Henriques JA. Braz. J. Med. Biol. Res. 2005; 38: 477
- 9j Haq IU. Lewitt PA. Fernandez HH. Expert Opin. Pharmacother. 2007; 8: 2799
- 9k Briganti A. Chun FK. Salonia A. Zanni G. Dehò F. Barbieri L. Karakiewicz P. Rigatti P. Montorsi F. Drugs Aging 2006; 23: 309
- 10a Stévigny C. Bailly C. Quetin-Leclercq J. Curr. Med. Chem.: Anti-Cancer Agents 2005; 5: 173
- 10b Nabavi SM. Uriarte E. Fontenla JA. Rastrelli L. Obarzo-Sanchez E. Curr. Org. Chem. 2017; 21: 342
- 11a Zhang A. Neumeyer JL. Baldessarini RJ. Chem. Rev. 2007; 107: 274
- 11b Antonini A. Tolosa E. Expert Rev. Neurother. 2009; 9: 859
- 12 Herraiz T. β-Carboline Alkaloids . In Bioactive Compounds in Foods . Gilbert J. Şenyuva HZ. Wiley-Blackwell; Oxford: 2009: 199
- 13 Smirnova OB. Golovko TV. Granik VG. Pharm. Chem. J. 2011; 45: 389
- 14a Zhang M. Sun D. Anti-Cancer Agents Med. Chem. 2015; 15: 537
- 14b Peduto A. More V. De Caprariis P. Festa M. Capasso A. Piacente S. De Martino L. De Feo V. Filosa R. Mini Rev. Med. Chem. 2011; 11: 486
- 15 Nafisi S. Bonsaii M. Maali P. Khalilzadeh MA. Manouchehri F. J. Photochem. Photobiol., B 2010; 100: 84
- 16a Song Y. Wang J. Teng SF. Kesuma D. Deng Y. Duan J. Wang JH. Qi RZ. Sim MM. Bioorg. Med. Chem. Lett. 2002; 12: 1129
- 16b Song Y. Kesuma D. Wang J. Deng Y. Duan J. Wang JH. Qi RZ. Biochem. Biophys. Res. Commun. 2004; 317: 128
- 16c Zhang J. Li Y. Guo L. Cao R. Zhao P. Jiang W. Wu J. Wang Y. Wu J. Cancer Biol. Ther. 2009; 8: 2374
- 17 Zhang X.-F. Sun R. Jia Y. Chen Q. Tu R.-F. Li K. Zhang X.-D. Du R.-L. Cao R. Sci. Rep. 2016; 6: 33204
- 18a Morikawa T. Sun B. Matsuda H. Wu LJ. Harima S. Yoshikawa M. Chem. Pharm. Bull. 2004; 52: 1194
- 18b Luo JG. Cao LH. Kong LY. Chin. Chem. Lett. 2012; 23: 1385
- 19a Stephens DN. Kehr W. Schneider HH. Schmiechen R. Neurosci. Lett. 1984; 47: 333
- 19b Stephens DN. Shearman GT. Kehr W. Psychopharmacology (Heidelberg, Ger.) 1984; 83: 233
- 19c Farzin D. Mansouri N. Eur. Neuropsychopharmacol. 2006; 16: 324
- 20a Bischler A. Napieralski B. Ber. Dtsch. Chem. Ges. 1893; 26: 1903
- 20b Heravi MM. Khaghaninejad S. Nazari N. Adv. Heterocycl. Chem. 2014; 112: 183
- 20c Heravi MM. Nazari N. Curr. Org. Chem. 2015; 19: 2358
- 21a Pictet A. Spengler T. Ber. Dtsch. Chem. Ges. 1911; 44: 2030
- 21b Dalpozzo R. Molecules 2016; 21: 699
- 21c Stöckigt J. Antonchick AP. Wu F. Waldmann H. Angew. Chem. Int. Ed. 2011; 50: 8538
- 21d Ingallina C. D’Acquarica I. Monache GD. Ghirga F. Quaglio D. Ghirga P. Berardozzi S. Markovic V. Botta B. Curr. Pharm. Des. 2016; 22: 1808
- 22a Zhu C. Wang R. Falck JR. Chem. Asian J. 2012; 7: 1502
- 22b Song G. Wang F. Li X. Chem. Soc. Rev. 2012; 41: 3651
- 23a Labinger JA. Bercaw JE. Nature (London) 2002; 417: 507
- 23b Chen X. Engle KM. Wang DH. Yu JQ. Angew. Chem. Int. Ed. 2009; 48: 5094
- 23c Gensch T. Hopkinson MN. Glorius F. Wencel-Delord J. Chem. Soc. Rev. 2016; 45: 2900
- 23d Moselage M. Li J. Ackermann L. ACS Catal. 2016; 6: 498
- 23e Knölker H.-J. Chem. Lett. 2009; 38: 8
- 23f You SL. Xia JB. Top. Curr. Chem. 2010; 292: 165
- 23g Yeung CS. Dong VM. Chem. Rev. 2011; 111: 1215
- 23h Sun CL. Li BJ. Shi ZJ. Chem. Rev. 2011; 111: 1293
- 23i Jia F. Li Z. Org. Chem. Front. 2014; 1: 194
- 23j Bauer I. Knölker H.-J. Chem. Rev. 2015; 115: 3170
- 24a Drost-Karbowska K. Acta Pol. Pharm. 1977; 34: 421
- 24b El-Shazly A. Wink M. Z. Naturforsch., C 2003; 58: 477
- 24c Battersby AR. Edwards TP. J. J. Chem. Soc. 1960; 1214
- 24d Taniyama D. Hasegawa M. Tomioka K. Tetrahedron Lett. 2000; 41: 5533
- 24e Werner F. Blank N. Opatz T. Eur. J. Org. Chem. 2007; 3911
- 24f Grajewska A. Rozwadowska MD. Tetrahedron: Asymmetry 2007; 18: 557
- 24g Zhu R. Xu Z. Ding W. Liu S. Shi X. Lu X. Chin. J. Chem. 2014; 32: 1039
- 24h Kaufman TS. Tetrahedron: Asymmetry 2004; 15: 1203
- 25a Zhang Q. Tu G. Zhao Y. Cheng T. Tetrahedron 2002; 58: 6795
- 25b Tunsag J. Davaakhuu G. Batsuren D. Mong. J. Chem. 2011; 12: 85 http://mongoliajol.info/index.php/MJC
- 25c Knölker H.-J. Agarwal S. Tetrahedron Lett. 2005; 46: 1173
- 25d Szawkało J. Zawadzka A. Wojtasiewicz K. Leniewski A. Drabowicz J. Czarnocki Z. Tetrahedron: Asymmetry 2005; 16: 3619
- 25e Meyer N. Opatz T. Eur. J. Org. Chem. 2006; 3997
- 25f Wu TR. Chong JM. J. Am. Chem. Soc. 2006; 128: 9647
- 25g Bailey KR. Ellis AJ. Reiss R. Snape TJ. Turner NJ. Chem. Commun. 2007; 3640
- 25h Louafi F. Moreau J. Shahane S. Golhen S. Roisnel T. Sinbandhit S. Hurvois J.-P. J. Org. Chem. 2011; 76: 9720
- 25i Gurram M. Gyimóthy B. Wang R. Lam SQ. Ahmed F. Herr RJ. J. Org. Chem. 2011; 76: 1605
- 25j Rotte SC. K. Chittiboyina AG. Khan IA. Eur. J. Org. Chem. 2013; 6355
- 25k Saha S. Reddy CB. R. Patro B. Tetrahedron Lett. 2011; 52: 4014
- 25l Kapat A. Kumar PS. Baskaran S. Beilstein J. Org. Chem. 2007; 3: 49
- 25m Pässler U. Knölker HJ. The Alkaloids: Chemistry and Biology . Vol. 70. Knölker HJ. Academic Press; New York: 2011: 79
- 26a Hughes DW. Skakum W. Genest K. J. Pharm. Sci. 1968; 57: 1023
- 26b Han Z. Zheng Y. Chen N. Luan L. Zhou C. Gan L. Wu Y. J. Chromatogr. A 2008; 1212: 76
- 26c Hirsenkorn R. Tetrahedron Lett. 1990; 31: 7591
- 26d Fossati E. Narcross L. Ekins A. Falgueyret JP. Martin VJ. PLoS One 2015; 10: e0124459
- 27 Aladesanmi AJ. Kelly CJ. Leary JD. J. Nat. Prod. 1983; 46: 127
- 28a Barton DH. R. Gunatilaka AA. L. Letcher RM. Lobo AM. F. T. Widdowson DA. J. Chem. Soc., Perkin Trans. 1 1973; 874
- 28b Tanaka H. Shibata M. Ito K. Chem. Pharm. Bull. 1984; 32: 1578
- 28c Tsuda Y. Nakai A. Ito K. Suzuki F. Haruna M. Heterocycles 1984; 22: 1817
- 28d Danishefsky SJ. Panek JS. J. Am. Chem. Soc. 1987; 109: 917
- 28e Ishibashi H. Sato T. Takahashi M. Hayashi M. Ikeda M. Heterocycles 1988; 27: 2787
- 28f Irie H. Shibata K. Matsuno K. Zhang Y. Heterocycles 1989; 29: 1033
- 28g Wasserman HH. Amici RM. J. Org. Chem. 1989; 54: 5843
- 28h Ishibashi H. Sato T. Takahashi M. Hayashi M. Ishikawa K. Ikeda M. Chem. Pharm. Bull. 1990; 38: 907
- 28i Tsuda Y. Sakai Y. Nakai A. Kaneko M. Ishiguro Y. Isobe K. Taga J. Sano T. Chem. Pharm. Bull. 1990; 38: 1462
- 28j Cassayre J. Quiclet-Sire B. Saunier JB. Zard SZ. Tetrahedron Lett. 1998; 39: 8995
- 28k Chikaoka S. Toyao A. Ogasawara M. Tamura O. Ishibashi H. J. Org. Chem. 2003; 68: 312
- 28l Wang Q. Padwa A. Org. Lett. 2006; 8: 601
- 28m Gao S. Tu YQ. Hu X. Wang S. Hua R. Jiang Y. Zhao Y. Fan X. Zhang S. Org. Lett. 2006; 8: 2373
- 28n Padwa A. Wang Q. J. Org. Chem. 2006; 71: 7391
- 28o Liang J. Chen J. Liu J. Li L. Zhang H. Chem. Commun. 2010; 46: 3666
- 28p Tuan LA. Kim G. Bull. Korean Chem. Soc. 2010; 31: 1800
- 28q Pan Z.-Q. Liang J.-X. Chen J.-B. Yang X.-D. Zhang H.-B. Nat. Prod. Bioprospect. 2011; 1: 129
- 28r Heller ST. Kiho T. Narayan AR. H. Sarpong R. Angew. Chem. Int. Ed. 2013; 52: 11129
- 28s Xu R.-Q. Gu Q. Wu W.-T. Zhao Z.-A. You S.-L. J. Am. Chem. Soc. 2014; 136: 15469
- 28t Paladino M. Zaifman J. Ciufolini MA. Org. Lett. 2015; 17: 3422
- 29a Leader K. Luwing B. Ruusa E. Acta Chem. Scand. 1969; 23: 244
- 29b Brossi A. Teitel S. Helv. Chim. Acta 1971; 54: 1564
- 29c Munchhof MJ. Meyers AI. J. Org. Chem. 1995; 60: 7086
- 29d Umetsu K. Asao N. Tetrahedron Lett. 2008; 49: 2722
- 29e Kurihara K. Yamamoto Y. Miyaura N. Adv. Synth. Catal. 2009; 351: 260
- 29f Yamato M. Hashigaki K. Qais N. Ishikawa S. Tetrahedron 1990; 46: 5909
- 29g Jiang T. Chen WW. Xu MH. Org. Lett. 2017; 19: 2138
- 29h Minor DL. Wyrick SD. Charifson PS. Watts VJ. Nichols DE. Mailman RB. J. Med. Chem. 1994; 37: 4317
- 30a Boit HG. Dçpke W. Naturwiss. Unterr. Chem. 1961; 48: 40
- 30b Wildman WC. The Alkaloids . Vol. II. Manske RH. F. Academic Press; New York: 1968: 308
- 30c Sanchez IH. Lopez FJ. Soria JJ. Larraza MI. Flores HJ. J. Am. Chem. Soc. 1983; 105: 7640
- 30d Stevens RV. Jun LE. D. J. Chem. Soc. D 1970; 1585
- 30e Hoshino O. Sawaki S. Shimamurai N. Onodera A. Umezawa B. Chem. Pharm. Bull. 1987; 35: 2734
- 30f Overman LE. Burk RM. Tetrahedron Lett. 1984; 25: 5739
- 30g Rousseau G. Lebeuf R. Schenk K. Castet F. Robert F. Landais Y. Chem. Eur. J. 2014; 20: 14771
- 30h Grundon MF. Nat. Prod. Rep. 1985; 2: 249
- 31 Lin W. Ma S. Org. Chem. Front. 2014; 1: 338
- 32 Battersby AR. Ramage R. Cameron AF. Hannaway C. Santavý F. J. Chem. Soc., Perkin Trans. 1 1971; 3514
- 33 Tojo E. Önür MA. Freyer AJ. Sharmma MJ. J. Nat. Prod. 1990; 53: 634
- 34 Freyer AJ. Abu Zarga MH. Firdous S. Guinaudeau H. Sharmma MJ. J. Nat. Prod. 1987; 50: 684
- 35 Meyers AI. Dickman DA. Boes M. Tetrahedron 1987; 43: 5095
- 36 Liu CJ. Liu DY. Xiang L. Yaoxue Xuebao 2010; 45: 9
- 37 Singh IP. Shah P. Expert Opin. Ther. Pat. 2017; 27: 17
- 38 Aladesanmi AJ. Ilesanmi OR. J. Nat. Prod. 1987; 50: 1041
- 39 Weller T. Koberstein R. Aissaoui H. Clozel M. Fischli W. WO 2005118548, 2005
- 40 Brisbare-Roch C. Dingemanse J. Koberstein R. Hoever P. Aissaoui H. Flores S. Mueller C. Nayler O. van Gerven J. de Haas SL. Hess P. Qiu C. Buchmann S. Scherz M. Weller T. Fischli W. Clozel M. Jenck F. Nat. Med. 2007; 13: 150
- 41 Singh IP. Bodiwala HS. Nat. Prod. Rep. 2010; 27: 1781
- 42 Wiart C. In Lead Compounds from Medicinal Plants for the Treatment of Cancer. Wiart C. Academic Press; San Diego: 2013: 35
- 43 Booth RG. In Foye’s Principles of Medicinal Chemistry . 7th ed.; Lemke TL. Williams DA. Roche VF. Zito SW. Lippincott Williams & Wilkins; Philadelphia: 2013: 430
- 44 Chang H.-M. In Methods in Lignin Chemistry . Lin SY. Dence CW. Springer; Heidelberg: 1992: 71
- 45 Tyne HL. Parsons J. Sinnott A. Fox SH. Fletcher NA. Steiger MJ. J. J. Neurol. 2004; 251: 1370
- 46a Shamma M. Slusarchyk WA. Chem. Rev. 1964; 64: 59
- 46b Melzer B. Bracher F. Org. Biomol. Chem. 2015; 13: 7664
- 46c Choi YL. Kim JK. Choi S.-U. Min Y.-K. Bae M.-A. Kim BT. Heo J.-N. Bioorg. Med. Chem. Lett. 2009; 19: 3036
- 46d Mukhtar MR. Hadi AH. A. Rondeau D. Richomme P. Litaudon M. Mustafa MR. Awang K. Nat. Prod. Lett. 2008; 22: 921
- 47 Hoshino O. Recent Developments on the Synthesis of Aporphine Alkaloids. In Studies in Natural Products Chemistry. Vol. 16, Part J. Atta-ur-Rahman Elsevier; Amsterdam: 1995: 503-546
- 48 Liu C.-M. Kao C.-L. Wu H.-M. Li WJ. Huang C.-T. Li HT. Chen C.-Y. Molecules 2014; 19: 17829
- 49 Rossini AF. C. Muraca AC. A. Casagrande GA. Raminelli C. J. Org. Chem. 2015; 80: 10033
- 50a Ye N. Wu Q. Zhu L. Zheng L. Gao B. Zhen X. Zhang A. Bioorg. Med. Chem. 2011; 19: 1999
- 50b Si YG. Choi YK. Gardner MP. Tarazi FI. Baldessarini RJ. Neumeyer JL. Bioorg. Med. Chem. Lett. 2009; 19: 51
- 50c Zhao R. Lu W. Fang X. Guo L. Yang Z. Ye N. Zhao J. Liu Z. Jia J. Zheng L. Zhao B. Zhang A. Zhen X. Pharmacol. Biochem. Behav. 2014; 124: 204
- 50d Munusamy V. Yap BK. Buckle MJ. Doughty SW. Chung LY. Chem. Biol. Drug Des. 2013; 81: 250
- 50e Ponnala S. Gonzales J. Kapadia N. Navarro NH. Harding WW. Bioorg. Med. Chem. Lett. 2014; 24: 1664
- 51 Zhang A. Zhang AY. Branfman AR. Baldessarini RJ. Neumeyer JL. J. Med. Chem. 2007; 50: 171
- 52 Sromek AW. Si Y.-G. Zhang T. George SR. Seeman P. Neumeyer JL. ACS Med. Chem. Lett. 2011; 2: 189
- 53 Zhang H. Ye N. Zhou S. Guo L. Zheng L. Liu Z. Gao B. Zhen X. Zhang A. J. Med. Chem. 2011; 54: 4324
- 54 Liu Z. Zhang H. Ye N. Zhang J. Wu Q.-Q. Sun P. Li L. Zhen X. Zhang A. J. Med. Chem. 2010; 53: 1319
- 55 Hughes DW. Genest K. Skakum W. J. Pharm. Sci. 1968; 57: 1619
- 56 Chiou C.-M. Lin C.-T. Huang W.-J. Chang Y.-M. Ho Y.-J. Su M.-J. Lee S.-S. J. Nat. Prod. 2013; 76: 405
- 57 Madapa S. Harding WW. J. Nat. Prod. 2015; 78: 722
- 58 Milián L. Ballesteros R. Sanz MJ. Blázquez MA. Med. Chem. Res. 2012; 21: 3133
- 59 Yang ZD. Zhang X. Du J. Ma ZJ. Guo F. Li S. Yao XJ. Nat. Prod. Res. 2012; 26: 387
- 60 Yang Z. Song Z. Xue W. Sheng J. Shu Z. Shi Y. Liang J. Yao X. Med. Chem. Res. 2014; 23: 3178
- 61 Callaway JC. J. Psychoact. Drugs 2005; 7: 151
- 62 Wadsworth AD. Naysmith BJ. Brimble MA. Eur. J. Med. Chem. 2015; 97: 816
- 63 Cao J. Xu Y. Kong Y. Cui Y. Hu Z. Wang G. Deng Y. Lai G. Org. Lett. 2012; 14: 38
- 64 Lee Y. Klausen RS. Jacobsen EN. Org. Lett. 2011; 13: 5564
- 65 Kumar AS. Nagarajan R. Org. Lett. 2011; 13: 1398
- 66 de la Fuente Revenga M. Pérez C. Morales-García JA. Alonso-Gil S. Pérez-Castillo A. Caignard D.-H. Yáñez M. Gamo AM. Rodríguez-Franco MI. ACS Chem. Neurosci. 2015; 6: 800
- 67 Onishi Y. Oishi K. Kawano Y. Yamazaki Y. Biosci. Rep. 2012; 32: 45
- 68 Farouk L. Laroubi A. Aboufatima R. Benharref A. Chait A. J. Ethnopharmacol. 2008; 115: 449
- 69a Haynes HF. Nelson ER. Price JR. Aust. J. Sci. Res., Ser. A 1952; 5: 387
- 69b Kanchanapoom T. Kasai R. Chumsri P. Hiraga Y. Yamasaki K. Phytochemistry 2001; 56: 383
- 69c Tanaka N. Momose R. Takahashi Y. Kubota T. Takahashi-Nakaguchi A. Gonoi T. Fromont J. Kobayashi J. Tetrahedron Lett. 2013; 54: 4038
- 69d Soriano-Agatón F. Lagoutte D. Poupon E. Roblot F. Fournet A. Gantier JC. Hocquemiller R. J. Nat. Prod. 2005; 68: 1581
- 69e Rosenkranz HJ. Botyos G. Schmid H. Justus Liebigs Ann. Chem. 1966; 691: 159
- 69f Czerwinski KM. Zificsak CA. Stevens J. Oberbeck M. Randlett C. King M. Mennen S. Synth. Commun. 2003; 33: 1225
- 69g Lindsley CW. Wisnoski DD. Wang Y. Leister WH. Zhao Z. Tetrahedron Lett. 2003; 44: 4495
- 69h Dai JK. Dan WJ. Li N. Du HT. Zhang JW. Wang JR. Bioorg. Med. Chem. Lett. 2016; 26: 580
- 69i Kim HM. Kim SJ. Kim HY. Ryu B. Kwak H. Hur J. Choi JH. Jang DS. Bioorg. Med. Chem. Lett. 2015; 25: 1017
- 69j Cebrian-Torrejon G. Domenech-Carbo A. Scotti MT. Fournet A. Figadere B. Poupon E. J. Mol. Struct. 2015; 1102: 242
- 69k Sasaki T. Li W. Higai K. Koike K. Bioorg. Med. Chem. Lett. 2015; 25: 1979
- 69l Showalter HD. H. J. Nat. Prod. 2013; 76: 455
- 69m Dai J. Li N. Wang J. Schneider U. Molecules 2016; 21: 493
- 70a Leboeuf M. Cavé A. Forgacs P. Provost J. Chiaroni A. Riche C. J. Chem. Soc., Perkin Trans. 1 1982; 1205
- 70b Costa EV. Pinheiro ML. B. Xavier CM. Silva JR. A. Amaral AC. F. Souza AD. L. Barison A. Campos FR. Ferreira AG. Machado GM. C. Leon LL. P. J. Nat. Prod. 2006; 69: 292
- 70c Costa EV. Pinheiro ML. B. Souza AD. L. Gama DA. S. Ramos CF. Ferreira AG. Barison A. Magn. Reson. Chem. 2008; 46: 69
- 70d Strödke B. Gehring AP. Bracher F. Arch. Pharm. (Weinheim, Ger.) 2015; 348: 125
- 70e Naik NH. Sikder AK. Kusurkar KS. Tetrahedron Lett. 2013; 54: 3715
- 70f Rejón-Orantes JC. González-Esquinca AR. de la Mora MP. Roldan Roldan G. Cortes D. Planta Med. 2011; 77: 322
- 70g See also ref. 70b
- 71a Kam T.-S. Sim K.-M. Phytochemistry 1998; 47: 145
- 71b Itoh T. Miyazaki M. Nagata K. Nakamura S. Ohsawa A. Heterocycles 2004; 63: 655
- 71c Knölke H.-J. Synlett 2004; 1767
- 71d Allin SM. Gaskell SN. Elsegood MR. J. Martin WP. Tetrahedron Lett. 2007; 48: 5669
- 71e Szawkało J. Czarnocki SJ. Zawadzka A. Wojtasiewicz K. Leniewski A. Maurin JK. Czarnocki Z. Drabowicz J. Tetrahedron: Asymmetry 2007; 18: 406
- 71f da Silva WA. Rodrigues Jr MT. Shankaraiah N. Ferreira RB. Andrade CK. Pilli RA. Santos LS. Org. Lett. 2009; 11: 3238
- 71g Huang D. Xu F. Lin X. Wang Y. Chem. Eur. J. 2012; 18: 3148
- 71h Sanaboina C. Jana S. Chidara S. Patro B. Raoljia GB. Eppakayal L. Tetrahedron Lett. 2012; 53: 5027
- 71i Lood SC. Koskinen AM. P. Eur. J. Org. Chem. 2014; 2357
- 71j Mondal P. Argade NP. Synthesis 2014; 46: 2591
- 71k Chakraborty I. Jana S. Synthesis 2013; 45: 3325
- 71l Lood SC. Koskinen AM. P. Chem. Heterocycl. Compd. 2015; 50: 1367
- 72a Wang K.-B. Di Y.-T. Bao Y. Yuan C.-M. Chen G. Li D.-H. Bai J. He H.-P. Hao X.-J. Pei J.-H. Jing YK. Li Z.-L. Hua H.-M. Org. Lett. 2014; 16: 4028
- 72b Carreira EM. Brandstätter M. Synfacts 2016; 12: 1113
- 72c Piemontesi C. Wang Q. Zhu J. J. Am. Chem. Soc. 2016; 138: 11148
- 73 Frost D. Meechoovet M. Wang T. Gately S. Giorgetti M. Shcherbakova I. Dunckley T. PLoS One 2011; 6: e19264
- 74a Beck O. Faull KF. Biochem. Pharmacol. 1986; 35: 2636
- 74b Cox ED. Cook JM. Chem. Rev. 1995; 95: 1797
- 74c Beck O. Jernström B. Martinez M. Repke DB. Chem. Biol. Interact. 1988; 65: 97
- 75 Tosuka Y. Ushiyama H. Ishihara J. Sinha R. Goto S. Sugimura T. Wakabayashi K. Cancer Lett. 1999; 143: 139
- 76a Patel K. Gadewar M. Tripathi R. Prasad SK. Patel DK. Asian Pac. J. Trop. Biomed. 2012; 660
- 76b Khan FA. Maalik A. Iqbal Z. Malik I. Eur. J. Pharmacol. 2013; 713: 391
- 76c Brierley DI. Davidson C. Prog. Neuro-Psychopharmacol. Biol. Psychiatry 2012; 39: 263
- 76d Niroumand MC. Farzaei MH. Amin G. J. Tradit. Chin. Med. 2015; 35: 104 https://www.journals.elsevier.com/journal-of-traditional-chinese-medicine/
- 77 Boursereau Y. Coldham I. Bioorg. Med. Chem. Lett. 2004; 14: 5841
- 78 Formagio AS. Tonin LT. D. Foglio MA. Madjarof C. Ernesto CJ. Ferreira CW. Cardoso FP. Sarragiotto MH. Bioorg. Med. Chem. 2008; 16: 9660
- 79 Cao R. Fan W. Guo L. Ma Q. Zhang G. Li J. Chen X. Ren Z. Qiu L. Eur. J. Med. Chem. 2013; 60: 135
- 80a McNulty J. Still IW. J. Curr. Org. Chem. 2000; 4: 121
- 80b Dong XC. Miao YP. Lin ZG. Yu F. Wen R. Acta Pharm. Sin. 2003; 38: 876
- 81a Wang WH. Nam SJ. Lee BC. Kang H. J. Nat. Prod. 2008; 71: 163
- 81b Badre A. Boulanger A. Abou-Mansour E. Banaigs B. Combaut G. Francisco C. J. Nat. Prod. 1994; 57: 528
- 81c Davis RA. Carroll AR. Quinn RJ. J. Nat. Prod. 1998; 61: 959
- 81d Lake RJ. Brennan MM. Blunt JW. Munro MH. G. Pannell LK. Tetrahedron Lett. 1988; 29: 2255
- 81e Ravinder K. Reddy AV. Krishnaiah P. Ramesh P. Ramakrishna S. Laatsch H. Venkateswarlu Y. Tetrahedron Lett. 2005; 46: 5475
- 82a Zhang G. Cao R. Guo L. Ma Q. Fan W. Chen X. Li J. Shao G. Qiu L. Ren Z. Eur. J. Med. Chem. 2013; 65: 21
- 82b Qifeng W. Rihui C. Manxiu F. Xiangdong G. Chunming M. Jinbing L. Huacan S. Wenlie P. Eur. J. Med. Chem. 2009; 44: 533
- 83 Resch V. Schrittwieser JH. Siirola E. Kroutil W. Curr. Opin. Biotechnol. 2011; 22: 793
- 84 Ravelli D. Protti S. Fagnoni M. Chem. Rev. 2016; 116: 9850
- 85 Mandal S. Mandal S. Ghosh SK. Ghosh A. Saha R. Banerjee S. Saha B. Synth. Commun. 2016; 46: 1327
- 86 Nising CF. Bräse S. Chem. Soc. Rev. 2012; 41: 988
- 87 Byrne PA. Gilheany DG. Chem. Soc. Rev. 2013; 42: 6670
- 88 Nicolaou KC. Snyder SA. Montagnon T. Vassilikogiannakis G. Angew. Chem. Int. Ed. 2002; 41: 1668
- 89 Jiménez-Osés G. Brockway AJ. Shaw JT. Houk KN. J. Am. Chem. Soc. 2013; 135: 6633
- 90 Bolm C. J. Org. Chem. 2012; 77: 5221
- 91 Li X. Leonori D. Sheikh NS. Coldham I. Chem. Eur. J. 2013; 19: 7724
- 92 Talk RA. Duperray A. Li X. Coldham I. Org. Biomol. Chem. 2016; 14: 4908
- 93 Miyazaki M. Ando N. Sugai K. Seito Y. Fukuoka H. Kanemitsu T. Nagata K. Odanaka Y. Nakamura KT. Itoh T. J. Org. Chem. 2011; 76: 534
- 94 Lin W. Cao T. Fan W. Han Y. Kuang J. Luo H. Miao B. Tang X. Yu Q. Yuan W. Zhang J. Zhu C. Ma S. Angew. Chem. Int. Ed. 2014; 53: 277
- 95 Lafrance M. Blaquiére N. Fagnou K. Chem. Commun. 2004; 2874
- 96 Chaudhary S. Pecic S. LeGendre O. Harding WW. Tetrahedron Lett. 2009; 50: 2437
- 97a Yamaguchi J. Yamaguchi AD. Itami K. Angew. Chem. Int. Ed. 2012; 51: 2
- 97b Allen SE. Walvoord RR. Padilla-Salinas R. Kozlowski RC. Chem. Rev. 2013; 113: 6234
- 98 Hellal M. Singh S. Cuny GD. Tetrahedron 2012; 68: 1674
- 99 Ku AF. Cuny GD. Org. Lett. 2015; 17: 1134
- 100 Ku AF. Cuny GD. J. Org. Chem. 2016; 81: 10062
- 101 Verniest G. England D. De Kimpe N. Padwa A. Tetrahedron 2010; 66: 1496
- 102 Ding S. Shi Z. Jiao N. Org. Lett. 2010; 12: 1540
- 103 June HL. Foster KL. McKay PF. Seyoum R. Woods II. JE. Harvey SC. Eiler WJ. A. II. Grey C. Carroll MR. McCane S. Jones CM. Yin W. Mason D. Cummings R. Garcia M. Ma C. Sarma PV. V. Cook JM. Skolnick P. Neuropsychopharmacology 2003; 28: 2124
- 104 Namjoshi OA. Gryboski A. Fonseca GO. Van Linn ML. Wang Z.-J. Deschamps JR. Cook JM. J. Org. Chem. 2011; 76: 4721
- 105 Phani Babu Tiruveedhula VV. N. Methuku KR. Deschamps JR. Cook JM. Org. Biomol. Chem. 2015; 13: 10705
- 106 Kawai N. Abe R. Matsuda M. Uenishi J. J. Org. Chem. 2011; 76: 2102
- 107 Reddy JR. Kawai N. Uenishi J. J. Org. Chem. 2012; 77: 11101
- 108 Teichert JF. Fañanás-Mastral M. Feringa BL. Angew. Chem. Int. Ed. 2011; 50: 688
- 109 Perrey DA. German NA. Decker AM. Thorn D. Li J.-X. Gilmour BP. Thomas BF. Harris DL. Runyon SP. Zhang Y. ACS Chem. Neurosci. 2015; 6: 599
- 110 Wenk HH. Winkler M. Sander W. Angew. Chem. Int. Ed. 2003; 42: 502
- 111 Hoye TR. Baire B. Niu D. Willoughby PH. Woods BP. Nature (London) 2012; 490: 208
- 112 Tadross PM. Stoltz BM. Chem. Rev. 2012; 112: 3550
- 113 Castedo L. Guitian E. Saá JM. Suau R. Tetrahedron Lett. 1982; 23: 457
- 114 Atanes N. Castedo L. Guitian E. Saá C. Saá JM. Suau R. J. Org. Chem. 1991; 56: 2984
- 115 Perecim GP. Rodrigues A. Raminelli C. Tetrahedron Lett. 2015; 56: 6848
- 116 Pulka K. Curr. Opin. Drug Discovery Dev. 2010; 13: 669
- 117 Mons E. Wanner MJ. Ingemann S. van Maarseveen JH. Hiemstra H. J. Org. Chem. 2014; 79: 7380
- 118 Liu Y. Song H. Huang Y. Li J. Zhao S. Song Y. Yang P. Xiao Z. Liu Y. Li Y. Shang H. Wang Q. J. Agric. Food Chem. 2014; 62: 9987
- 119 Dong J. Shi X.-X. Yan J.-J. Xing J. Zhang Q. Xiao S. Eur. J. Org. Chem. 2010; 6987
- 120 Eagon S. Anderson MO. Eur. J. Org. Chem. 2014; 1653
- 121 Kamal A. Tangella Y. Manasa KL. Sathish M. Srinivasulu V. Chetna J. Alarifi A. Org. Biomol. Chem. 2015; 13: 8652
- 122 Sodaeizadeh H. Rafieiolhossaini M. Havlík J. van Damme P. Plant Growth Regul. 2009; 59: 227
- 123 Weng Q. Huang J. Zeng Y. Deng Y. Hu M. Molecules 2012; 17: 3969
- 124 Chen H. Gao P. Zhang M. Liao W. Zhang J. New J. Chem. 2012; 38: 4155
- 125 Gohil VM. Brahmbhatt KG. Loiseau PM. Bhutani KK. Bioorg. Med. Chem. Lett. 2012; 22: 3905
- 126 Chauhana SS. Singh AK. Meena S. Lohani M. Singh A. Arya RK. Cheruvu SH. Sarkar J. Gayen JR. Datta D. Chauhan PM. S. Bioorg. Med. Chem. Lett. 2014; 24: 2820
- 127 Kamal A. Manda S. Avasarala VG. P. Jadala C. Tangella Y. Srinivasulu V. Nagula S. Alarifi A. RSC Adv. 2015; 5: 90121
- 128 Panarese JD. Waters SP. Org. Lett. 2010; 12: 4086
- 129 Nissen F. Richard V. Alayrac C. Witulski B. Chem. Commun. 2011; 47: 6656
- 130 Yamaguchi AD. Mandal D. Yamaguchi J. Itami K. Chem. Lett. 2011; 40: 555
- 131 Roggero CM. Giulietti JM. Mulcahy SP. Bioorg. Med. Chem. Lett. 2014; 24: 3549
- 132 Schupp P. Poehner T. Edrada A. Ebel R. Berg A. Wray V. Proksch P. J. Nat. Prod. 2003; 66: 272
- 133 Finlayson R. Brackovic A. Simon-Levert A. Banaigs B. O’Toole RF. Miller CH. Copp BR. Tetrahedron Lett. 2011; 52: 837
- 134 Won TH. Jeon J. Lee S. Rho BJ. Oh K. Shin J. Bioorg. Med. Chem. 2012; 20: 4082
- 135 Battini N. Padala AK. Mupparapu N. Vishwakarma RA. Ahmed AN. RSC Adv. 2014; 4: 26258
- 136 Eftekhari-Sis B. Zirak M. Akbari A. Chem. Rev. 2013; 113: 2958
- 137 Panarese JD. Waters SP. Org. Biomol. Chem. 2013; 11: 3428
- 138 Trieu TH. Dong J. Zhang Q. Zheng B. Meng T.-Z. Lu X. Shi X.-X. Eur. J. Org. Chem. 2013; 3271
- 139 Jin H. Zhang P. Bijian K. Ren S. Wan S. Alaoui-Jamali MA. Jiang T. Mar. Drugs 2013; 11: 1427
- 140 Zhu Y.-P. Liu M.-C. Cai Q. Jia F.-C. Wu A.-X. Chem. Eur. J. 2013; 19: 10132
- 141 Zhang PY. Wang JL. Wan SB. Jiang T. Chin. Chem. Lett. 2010; 21: 889
- 142 Zhang PY. Wan SB. Ren SM. Jiang T. Chin. Chem. Lett. 2010; 21: 1307
- 143 Liew LP. P. Fleming JM. Longeon A. Mouray E. Florent I. Bourguet-Kondracki ML. Copp BR. Tetrahedron 2014; 70: 4910
- 144 Meruva SB. Raghunadh A. Kamaraju RR. Kumar UK. S. Dubey PK. Beilstein J. Org. Chem. 2014; 10: 471
- 145 Barolo SM. Teng X. Cuny GD. Rossi RA. J. Org. Chem. 2006; 71: 8493
- 146 Song H. Liu Y. Liu Y. Wang L. Wang Q. J. Agric. Food Chem. 2014; 62: 1010
- 147 Luo W. Liu J. Li J. Zhang D. Liu M. Addo JK. Patil S. Zhang L. Yu J. Buolamwini JK. Chen J. Huang C. J. Biol. Chem. 2008; 283: 8624
- 148 Yang X. Wang W. Qin J.-J. Wang MH. Sharma H. Bolamwini JK. Wang H. Zhang R. PLoS One 2012; 7: e34303
- 149 Filali I. Bouajila J. Znati M. Bousejra-El Garah F. Jannet HB. J. Enzyme Inhib. Med. Chem. 2015; 30: 371
- 150 Schumacher M. Kelkel M. Dicato M. Diederich M. Biotech. Adv. 2011; 29: 531
- 151 Yasuhara-Bell J. Lu Y. Antiviral Res. 2010; 86: 231
- 152 Vo T.-S. Ngo D.-H. Ta QV. Kim S.-K. Eur. J. Pharm. Sci. 2011; 44: 11
- 153 De Jong S. Nosal DG. Wardrop DJ. Tetrahedron 2012; 68: 4067
- 154 Zhang M.-Z. Chen Q. Yang GF. Eur. J. Med. Chem. 2015; 89: 421
- 155 Bonazzi S. Barbaras D. Patiny L. Scopelliti R. Schneider P. Cole ST. Kaiser M. Brun R. Gademann K. Bioorg. Med. Chem. 2010; 18: 1464
- 156 Diaz-Sylvester PL. Porta M. Juettner VV. Lv Y. Fleischer S. Copello JA. Mol. Pharmacol. 2014; 85: 564
Noscapine. Isolation:
https://www.hindawi.com/journals/jchem/ Synthesis:
Biological properties:
Reviews:
Solifenacin. Synthesis:
Biological properties:
Reviews:
Almorexant. Synthesis:
Biological properties:
Review:
Metatacarbolines A and C. Isolation:
Synthesis:
Dichotomines A–D. Isolation:
Synthesis:
Harmala alkaloids (harman, harmine, harmol, harmalan, harmaline, harmalol). Isolation:
Synthesis:
Biological activities:
Reviews:
Apomorphine. Isolation:
Synthesis:
Biological properties:
Reviews:
(S)-Salsolidine. Isolation:
Synthesis:
Review:
Crispine. Isolation:
Synthesis:
Review:
(S)-Reticuline. Isolation:
Synthesis:
3-Demethoxyerythratidinone. Isolation:
Synthesis:
Cryptostyline. Isolation:
Synthesis:
Biological properties:
epi-Elwesine. Isolation:
Synthesis:
Review:
Canthin-6-one. Isolation:
Synthesis:
Biological properties:
Reviews:
Annomontine. Isolation:
Synthesis:
Biological properties:
Harmicine, Isolation:
Synthesis:
Reviews:
(+)-Peganumine A. Isolation:
Synthesis:
Reviews covering the biological properties of carbolines: