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DOI: 10.1055/s-0032-1316918
Palladium-Mediated Total Synthesis of Bioactive Natural Products
Publication History
Received: 22 January 2013
Accepted after revision: 14 February 2013
Publication Date:
25 April 2013 (online)
![](https://www.thieme-connect.de/media/synthesis/201310/lookinside/thumbnails/10.1055-s-0032-1316918-1.jpg)
This review article is dedicated to my teacher Professor S. K. Talapatra of Calcutta University on the occasion of his 80th birthday
Abstract
The search for efficient synthetic procedures for natural products, drugs, and materials with economical and ecological advantages is an important area of current interst in synthetic organic chemistry. We have made an attempt to summarize the progress made in this area since 2005. This article describes the syntheses of several natural products and drugs that employ multiple palladium-catalyzed processes in either a sequential or a domino fashion.
1 Introduction
2 Palladium-Mediated Synthesis of Alkaloids
2.1 Indole Alkaloids
2.2 Carbazole Alkaloids
2.3 Quinoline and Isoquinoline Alkaloids
2.4 Pyrrole and Pyridine Alkaloids
2.5 Pyrrolizidine and Indolizidine Alkaloids
2.6 Imidazole and Guanidine Alkaloids
2.7 Other Alkaloids
3 Palladium-Mediated Synthesis of Natural Products Containing a Sugar Moiety
4 Palladium-Mediated Synthesis of Marine Natural Products
5 Palladium-Mediated Synthesis of Amino Acids and Peptides
6 Palladium-Mediated Synthesis of Terpenoids
7 Miscellaneous Natural Products
8 Conclusion
-
Reference
- 1a Heterocycles in Natural Product Synthesis . Majumdar KC, Chattopadhyay SK. Wiley-VCH; Weinheim: 2011
- 1b Eicher T, Hauptmann S. The Chemistry of Heterocycles: Structure, Reactions, Synthesis and Applications. Wiley-VCH; Weinheim: 2003
- 1c Tadross PM, Stoltz BM. Chem. Rev. 2012; 112: 3550
- 2 Gladysz JA. Chem. Rev. 2005; 105: 4235
- 3a Majumdar KC, Samanta S, Sinha B. Synthesis 2012; 44: 817
- 3b Majumdar KC, Chattopadhyay B, Maji P, Chattopadhyay SK, Samanta S. Heterocycles 2010; 81: 517
- 3c Majumdar KC, Chattopadhyay B, Maji P, Chattopadhyay SK, Samanta S. Heterocycles 2010; 81: 795
- 3d Yin X, Liebscher J. Chem. Rev. 2007; 107: 133
- 4a Bras JL, Muzart J. Chem. Rev. 2011; 111: 1170
- 4b Carsten B, He F, Son HJ, Xu T, Yu L. Chem. Rev. 2011; 111: 1493
-
4c Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417
-
4d Chinchilla R, Nájera C. Chem. Rev. 2007; 107: 874
-
4e Negishi E, Anastasia L. Chem. Rev. 2003; 103: 1979
- 4f Weaver JD, Recio A, Grenning AJ, Tunge JA. Chem. Rev. 2011; 111: 1846
-
5a Edmonds DJ, Johnston D, Procter DJ. Chem. Rev. 2004; 104: 3371
- 5b Takao K, Munakata R, Tadano K. Chem. Rev. 2005; 105: 4779
- 5c Touré BB, Hall DG. Chem. Rev. 2009; 109: 4439
- 5d Song J.-L, Fan C.-A, Tu Y.-Q. Chem. Rev. 2011; 111: 7523
-
6a Dounay AB, Overman LE. Chem. Rev. 2003; 103: 2945
- 6b Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
- 6c Tietze LF, Düfert A. Pure Appl. Chem. 2010; 82: 1375
- 7a Fukuda T, Sudo E, Shimokawa M. Tetrahedron 2008; 64: 328
- 7b Fujikawa N, Ohta T, Yamaguchi T, Fukuda T, Ishibashi F, Iwao M. Tetrahedron 2006; 62: 594
- 7c Koch K, Podlech J, Pfeiffer E, Metzler M. J. Org. Chem. 2005; 70: 3275
-
7d Trost BM, Zhang T. Angew. Chem. Int. Ed. 2008; 47: 3759
- 7e Shie J.-J, Fang J.-M, Wong C.-H. Angew. Chem. Int. Ed. 2008; 47: 5788
- 7f Prediger P, Barbosa LF, Genisson Y, Correia CR. D. J. Org. Chem. 2011; 76: 7737
- 7g Boglio C, Stahlke S, Thorimbert S, Malacria M. Org. Lett. 2005; 7: 4851
- 7h Wu M.-J, Lee C.-L, Wu Y.-C, Chen C.-P. Eur. J. Org. Chem. 2008; 854
- 7i Levine SR, Krout MR, Stoltz BM. Org. Lett. 2009; 11: 289
- 8a Movassaghi M, Ondrus AE. Org. Lett. 2005; 7: 4423
- 8b Keck D, Vanderheiden S, Bräse S. Eur. J. Org. Chem. 2006; 4916
- 8c Chavan SP, Pathak AB, Kalkote UR, Bringmann G, Rudenauer S, Bruhn T, Benson L, Brun R. Tetrahedron 2008; 64: 5563
- 8d Markey MD, Kelly TR. Org. Lett. 2007; 9: 3255
- 8e Kitawaki T, Hayashi Y, Ueno A, Chida N. Tetrahedron 2006; 62: 6792
- 8f Forke R, Jager A, Knölker H.-J. Org. Biomol. Chem. 2008; 6: 2481
- 8g Borger C, Knölker H.-J. Synlett 2008; 1698
- 8h Hirao S, Yoshinaga Y, Iwao M, Ishibashi F. Tetrahedron Lett. 2010; 51: 533
- 8i Fürstner A, Domostoj MM, Scheiper B. J. Am. Chem. Soc. 2006; 128: 8087
- 8j Karadeolian A, Kerr MA. J. Org. Chem. 2010; 75: 6830
- 8k Banwell MG, Lupton DW. Org. Biomol. Chem. 2005; 3: 213
- 8l Trost BM, Stiles DT. Org. Lett. 2007; 9: 2763
- 8m Chen J.-Q, Xie J.-H, Bao D.-H, Liu S, Zhou Q.-L. Org. Lett. 2012; 14: 2714
- 8n Bowie AL, Trauner D. J. Org. Chem. 2009; 74: 1581
- 9a Ninomiya I, Kiguchi T In The Alkaloids . Vol. 38. Brossi A. Academic Press; San Diego: 1990: 1
- 9b Somei M, Yokoyama Y, Murakami Y, Ninomiya I, Kiguchi T, Naito T. In The Alkaloids . Vol. 54. Cordell GA. Academic Press; San Diego: 2000: 191
- 10 Xu Z, Li Q, Zhang L, Jia Y. J. Org. Chem. 2009; 74: 6859
- 11a Inuki S, Oishi S, Fujii N, Ohno H. Org. Lett. 2008; 10: 5239
-
11b Inuki S, Iwata A, Oishi S, Fujii N, Ohno H. J. Org. Chem. 2011; 76: 2072
- 12 Iwata A, Inuki S, Oishi S, Fujii N, Ohno H. J. Org. Chem. 2011; 76: 5506
- 13a Kato L, Braga RM, Koch I, Kinoshita LS. Phytochemistry 2002; 60: 315
- 13b Braga RM, Reis FA. M. Phytochemistry 1987; 26: 833
- 14a Yu J, Wearing XZ, Cook JM. J. Org. Chem. 2005; 70: 3963
- 14b Zhou H, Liao X, Yin W, Ma J, Cook JM. J. Org. Chem. 2006; 71: 251
- 15 de Fatima M, Batina C, Cintra AC. O, Veronese EL. G, Lavrador MA. S, Giglio JR, Pereira PS, Dias DA, Franca SC, Sampaio SV. Planta Med. 2000; 66: 424
- 16 Larock RC, Yum EK. J. Am. Chem. Soc. 1991; 113: 6689
- 17 Trost BM, McDougall PJ. Org. Lett. 2009; 11: 3782
- 18 Bhat V, Allan KM, Rawal VH. J. Am. Chem. Soc. 2011; 133: 5798
- 19a Smith CD, Zilfou JT, Stratmann K, Patterson GM. L, Moore RE. Mol. Pharmacol. 1995; 47: 241
- 19b Zhang X, Smith CD. Mol. Pharmacol. 1996; 49: 288
- 20 Bonjoch J, Sole D. Chem. Rev. 2000; 100: 3455
- 21 Le Men J, Taylor WI. Experientia 1965; 21: 508
- 22a Eichberg MJ, Dorta RL, Grotjahn DB, Lamottke K, Schmidt M, Vollhardt KP. C. J. Am. Chem. Soc. 2001; 123: 9324
- 22b Nakanishi M, Mori M. Angew. Chem. Int. Ed. 2002; 41: 1934
- 23a Mori M, Nakanishi M, Kajishima D, Sato Y. J. Am. Chem. Soc. 2003; 125: 9801
- 23b Ohshima T, Xu Y, Takita R, Shibasaki M. Tetrahedron 2004; 60: 9569
- 23c Kaburagi Y, Tokuyama H, Fukuyama T. J. Am. Chem. Soc. 2004; 126: 10246
- 24a Zhang H, Boonsombat J, Padwa A. Org. Lett. 2007; 9: 279
- 24b Boonsombat J, Zhang H, Chughtai MJ, Hartung J, Padwa A. J. Org. Chem. 2008; 73: 3539
- 24c Beemelmanns C, Reissig H.-U. Angew. Chem. Int. Ed. 2010; 49: 8021
- 24d Sirasani G, Paul T, Dougherty W, Kassel S, Andrade RB. J. Org. Chem. 2010; 75: 3529
- 25a Massiot G, Thépenier P, Jacquier M.-J, Le Men-Olivier L, Delaude C. Heterocycles 1989; 29: 1435
- 25b Higuchi K, Kawasaki T. Nat. Prod. Rep. 2007; 24: 843
-
26 Dounay AB, Humphreys PG, Overman LE, Wrobleski AD. J. Am. Chem. Soc. 2008; 130: 5368
- 27 Snell RH, Woodward RL, Willis MC. Angew. Chem. Int. Ed. 2011; 50: 9116
- 28 Jannic V, Guritte F, Laprvote O, Serani L, Martin M, Senet T, Potier P. J. Nat. Prod. 1999; 62: 838
- 29 Verotta L, Orsini F, Sbacchi M, Scheildler MA, Amador TA, Elisabetsky E. Bioorg. Med. Chem. 2002; 10: 2133
- 30a Knölker H.-J. Curr. Org. Synth. 2004; 1: 309
- 30b Fröhner W, Krahl MP, Reddy KR, Knölker H.-J. Heterocycles 2004; 63: 2393
- 30c Krahl MP, Jäger A, Krause T, Knölker H.-J. Org. Biomol. Chem. 2006; 4: 3215
- 30d Knölker H.-J, Reddy KR. Chem. Rev. 2002; 102: 4303
- 30e Agarwal S, Cämmerer S, Filali S, Fröhner W, Knöll J, Krahl MP, Reddy KR, Knölker H.-J. Curr. Org. Chem. 2005; 9: 1601
- 30f Knölker H.-J. Chem. Lett. 2009; 38: 8
- 30g Bauer I, Knölker H.-J. Top. Curr. Chem. 2012; 309: 203
- 30h Schmidt AW, Reddy KR, Knölker H.-J. Chem. Rev. 2012; 112: 3193
- 31a Knölker H.-J. Tetrahedron 2012; 68: 6727
- 31b Knölker H.-J, Bauermeister M. J. Chem. Soc., Chem. Commun. 1990; 664
- 31c Knölker H.-J, Bauermeister M. Tetrahedron 1993; 48: 11221
- 31d Börger C, Kataeva O, Knölker H.-J. Org. Biomol. Chem. 2012; 10: 7269
- 31e Knölker H.-J, Bauermeister M. J. Indian Chem. Soc. 1994; 71: 345
- 31f Forke R, Krahl MP, Däbritz F, Jäger F, Knölker H.-J. Synlett 2008; 1870
- 31g Alayrac C, Schollmeyer D, Witulski B. Chem. Commun. 2009; 1464
- 31h Knott KE, Auschill S, Jäger A, Knölker H.-J. Chem. Commun. 2009; 1467
- 32 Wu T.-S, Wang M.-L, Wu P.-L. Phytochemistry 1996; 43: 785
- 33 Gruner KK, Knölker H.-J. Org. Biomol. Chem. 2008; 6: 3902
- 34 Cannon JR, Croft KD, Matsuki Y, Patrick VA, Toia RF, White AH. Aust. J. Chem. 1982; 35: 1655
- 35a Goldberg AF. G, Stoltz BM. Org. Lett. 2011; 13: 4474
-
35b Shimizu I, Ohashi Y, Tsuji J. Tetrahedron Lett. 1985; 26: 3825
- 36 Dijk EW, Panella L, Pinho P, Naasz R, Meetsma A, Minnaard AJ, Feringa BL. Tetrahedron 2004; 60: 9687
- 37 Saeki M, Toyota M. Tetrahedron Lett. 2010; 51: 4620
- 38a Gözler B. Pavine and Isopavine Alkaloids. In The Alkaloids . Vol. 31. Brossi A. Academic Press; New York: 1987: 317
- 38b Shinohara T, Takeda A, Toda J, Sano T. Heterocycles 1998; 48: 981
- 39a Weber E, Keana J, Barmettler P. PCT Int. Appl. WO 9012575, 1990 ; Chem. Abstr. 1991, 115, 106019.
- 39b Childers Jr WE, Abou-Gharbia MA. U.S. Patent 4,940,789, 1990 ; Chem. Abstr. 1990, 113, 191190.
- 40 Tamber UK, Ebner DC, Stoltz BM. J. Am. Chem. Soc. 2006; 128: 11752
- 41a Trost BM, Dong G. Chem. Eur. J. 2009; 15: 6910
- 41b Trost BM, Dong G. J. Am. Chem. Soc. 2006; 126: 6054
- 42 Ambrosio MD, Guerriero A, Debitus C, Ribes O, Pusset J, Leroy S, Pietra F. J. Chem. Soc., Chem. Commun. 1993; 1305
- 43 Pettit GR, Ducki S, Herald DL, Doubek DL, Schmidt JM, Chapuis JC. Oncol. Res. 2005; 15: 11
- 45 Narasaka K, Kitamura M. Eur. J. Org. Chem. 2005; 4505
- 46 Fürstner A, Radkowski K, Peters H, Seidel G, Wirtz C, Ynott RM, Lehmann CW. Chem. Eur. J. 2007; 13: 1929
- 47a Jayasuriya H, Herath KB, Ondeyka JG, Polishook JD, Bills GF, Dombrowski AW, Springer MS, Siciliano S, Malkowitz L, Sanchez M, Guan ZQ, Tiwari S, Stevenson DW, Borris RP, Singh SB. J. Nat. Prod. 2004; 67: 1036
- 47b Klausmeyer P, Chmurny GN, McCloud TG, Tucker KD, Shoemaker RH. J. Nat. Prod. 2004; 67: 1732
- 48 Li G, Watson K, Buckheit RW, Zhang Y. Org. Lett. 2007; 9: 2043
- 49 Fairlamb IJ. S, Marrison LR, Dickinson JM, Lu F.-J, Schmidt JP. Bioorg. Med. Chem. 2004; 12: 4285
- 50 Zhang F, Zaidi S, Haney KM, Kellogg GE, Zhang Y. J. Org. Chem. 2011; 76: 7945
- 51 Molyneaux RJ, Benson M, Wong RY, Tropea JE, Elbein AD. J. Nat. Prod. 1988; 51: 1198
- 54 Trost BM, Aponick A, Stanzl BN. Chem. Eur. J. 2007; 13: 9547
- 55 Ishibashi H, Sasaki M, Taniguchi T. Tetrahedron 2008; 64: 7771
- 56 Couty S, Meyer C, Cossy J. Tetrahedron 2009; 65: 1809
- 57 Nicolai S, Piemontesi C, Waser J. Angew. Chem. Int. Ed. 2011; 50: 4680
- 58 Djerassi C, Kutney JP, Shamma M. Tetrahedron 1962; 18: 183
- 59 Takeda K, Toyota M. Tetrahedron Lett. 2011; 52: 5872
- 60 Guo H, O’Doherty GA. Org. Lett. 2006; 8: 1609
-
61 Sears P, Wong C.-H. Angew. Chem. Int. Ed. 1999; 38: 2300
- 62a Takishima S, Ishiyama A, Iwatsuki M, Otoguro K, Yamada H, Omura S, Kobayashi H, van Soest RW. M, Matsunaga S. Org. Lett. 2009; 11: 2655
- 62b Takishima S, Ishiyama A, Iwatsuki M, Otoguro K, Yamada H, Omura S, Kobayashi H, van Soest RW. M, Matsunaga S. Org. Lett. 2010; 12: 896
- 63 Aron ZD, Overman LE. Chem. Commun. 2004; 253
- 64a Arnold MA, Day KA, Duron SG, Gin DY. J. Am. Chem. Soc. 2006; 128: 13255
- 64b Butters M, Davies CD, Elliott MC, Hill-Cousins J, Kariuki BM, Ooi L.-L, Wood JL, Wordingham SV. Org. Biomol. Chem. 2009; 7: 5001
- 65 Evans PA, Qin J, Robinson JE, Bazin B. Angew. Chem. Int. Ed. 2007; 46: 7417; Angew. Chem. 2007, 119, 7561
- 66 Babij NR, Wolfe JP. Angew. Chem. Int. Ed. 2012; 51: 4128
- 67 Davies SG, Roberts PM, Stephenson PT, Storr HR, Thomson JE. Tetrahedron 2009; 65: 8283
- 68 Talyor P. In The Pharmacological Basis of Therapeutics . 6th ed.; Gilman AG, Goodman LS, Gilman A. Macmillan; New York: 1980
- 69a Abe T, Ikeda T, Yanada R, Ishikura M. Org. Lett. 2011; 13: 3356
- 69b Abe T, Ikeda T, Choshi T, Hibino S, Hatae N, Toyata E, Yanada R, Ishikura M. Eur. J. Org. Chem. 2012; 5018
- 70a Rickards RW, Rothschild JM, Willis AC, de Chazal NM, Kirk J, Kirk K, Saliba KJ, Smith GD. Tetrahedron 1999; 55: 13513
- 70b Bernardo PH, Chai CL. L, Heath GA, Mahon PJ, Smith GD, Waring P, Wilkes BA. J. Med. Chem. 2004; 47: 4958
- 71 Khan QA, Lu J, Hecht SM. J. Nat. Prod. 2009; 72: 438
- 72 Ishikura M. Heterocycles 2011; 83: 247
- 73a Vavreckova C, Gawlik I, Muller K. Planta Med. 1996; 62: 397
- 73b Schemeller T, Latz-Bruning B, Wink M. Phytochemistry 1997; 44: 257
- 73c Huang F.-C, Kutchan TM. Phytochemistry 2000; 53: 555
- 74 Nakanishi T, Suzuki M. J. Nat. Prod. 1998; 61: 1263
- 75 Lv P, Huang K, Xie L, Xu X. Org. Biomol. Chem. 2011; 9: 3133
- 76a Wu P.-L, Rao KV, Su C.-H, Kuoh C.-S, Wu T.-S. Heterocycles 2002; 57: 2401
- 76b Ratnagiriswaran AN, Venkatachalam K. J. Med. Res. 1935; 22: 433
- 77a Yang X, Shi Q, Liu Y.-N, Zhao G, Bastow KF, Lin J.-C, Yang S.-C, Yang P.-C, Lee K.-H. J. Med. Chem. 2009; 52: 5262
- 77b Gao W, Chen AP.-C, Leung C.-H, Gullen EA, Furstner A, Shi Q, Wei L, Lee K.-H, Cheng Y.-C. Bioorg. Med. Chem. Lett. 2008; 18: 704
- 77c Banwell MG, Bezos A, Burns C, Kruszelnicki I, Parish CR, Su S, Sydnes MO. Bioorg. Med. Chem. Lett. 2006; 16: 181
- 78 Rossiter LM, Slater ML, Giessert RE, Sakwa SA, Herr RJ. J. Org. Chem. 2009; 74: 9554
- 79a González-Gálvez D, García-García E, Alibés R, Bayón P, de March P, Figueredo M, Font J. J. Org. Chem. 2009; 74: 6199
- 79b Alibés R, Bayón P, de March P, Figueredo M, Font J, García-García E, González-Gálvez D. Org. Lett. 2005; 7: 5107
- 80a Bayón P, Busque F, Figueredo M. Targets Heterocycl. Syst. 2005; 9: 281
- 80b Weinreb SM. Nat. Prod. Rep. 2009; 26: 758
- 81a Abe N, Nakakita Y, Nakamura T, Enoki N, Uchida H, Takeo T, Munekata M. J. Antibiot. 1993; 46: 1672
- 81b Fang YA, Linardic CM, Richardson DA, Behforouz MA. Mol. Cancer Ther. 2003; 2: 517
- 81c Love BE. Top. Heterocycl. Chem. 2006; 2: 93
- 82 Nissen F, Detert H. Eur. J. Org. Chem. 2011; 2845
- 83a Zhang B, Higuchi R, Miyamoto T, Soest RW. M. V. Chem. Pharm. Bull. 2008; 56: 866
- 83b Baldwin JE, Claridge TD. W, Culshaw AJ, Heupel FA, Lee V, Spring DR, Whitehead RC. Chem. Eur. J. 1999; 5: 3154
- 84 Jakubec P, Hawkins A, Felzmann W, Dixon DJ. J. Am. Chem. Soc. 2012; 134: 17482
- 85 Brachman PS, Kaufmann AF In Bacterial Infections of Humans . Evans AS, Brachman PS. Plenum Medical Book Company; New York: 1998: 95
- 86a Nicholson WL, Munakata N, Horneck G, Melosh HJ, Setlow P. Microbiol. Mol. Biol. Rev. 2000; 64: 548
- 86b Moayeri M, Leppla SH. Curr. Opin. Microbiol. 2004; 7: 19
- 86c Werz DB, Seeberger PH. Angew. Chem. Int. Ed. 2005; 44: 6315; Angew. Chem. 2005, 117, 6474
- 87a Daubenspeck JM, Zeng H, Chen P, Dong S, Steichen CT, Krishna NR, Pritchard DG, Turnbough CL. J. Biol. Chem. 2004; 279: 30945
- 87b Tamborrini M, Werz DB, Frey J, Pluschke G, Seeberger PH. Angew. Chem. Int. Ed. 2006; 45: 6581; Angew. Chem. 2006, 118, 6731
- 88 Guo H, O’Doherty GA. Angew. Chem. Int. Ed. 2007; 46: 5206
- 89 Guo H, O’Doherty GA. J. Org. Chem. 2008; 73: 5211
- 90a Wu B, Li M, O’Doherty GA. Org. Lett. 2010; 12: 5466
- 90b Shi P, Silva M, Wu B, Wang H.-YL, Akhmedov NG, Li M, Beuning P, O’Doherty GA. ACS Med. Chem. Lett. 2012; 3: 1086
- 91 Greeff K. Cardiac Glycosides, Part 1: Experimental Pharmacology. In Handbook of Experimental Pharmacology. Vol. 56. Springer-Verlag; Berlin/New York: 1981
- 92 Bocknack BM, Wang L.-C, Krische MJ. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 5421
- 93 Tiwari KN, Khare NK, Khare A, Khare MP. Carbohydr. Res. 1984; 129: 179
- 94a Zhou M, O’Doherty GA. J. Org. Chem. 2007; 72: 2485
- 94b Zhou M, O’Doherty GA. Org. Lett. 2006; 8: 4339
- 95a Traxler P, Gruner J, Auden JA. J. Antibiot. 1977; 30: 289
- 95b Traxler P, Fritz H, Fuhrer H, Richter W. J. Antibiot. 1980; 33: 967
- 96a Ahmed M, O’Doherty GA. Tetrahedron Lett. 2005; 46: 4151
- 96b Balachari D, O’Doherty GA. Org. Lett. 2000; 2: 4033
- 96c Balachari D, O’Doherty GA. Org. Lett. 2000; 2: 863
- 96d Denmark SC, Regens CS, Kobayashi T. J. Am. Chem. Soc. 2007; 129: 2774
- 96e Denmark SC, Kobayashi T, Regens CS. Tetrahedron 2010; 66: 4745
- 97a Chien S.-C, Young PH, Hsu Y.-J, Chen C.-H, Tien Y.-J, Shiu S.-Y, Li T.-H, Yang C.-W, Marimuthu P, Tsai LF.-L, Yang W.-C. Phytochemistry 2009; 70: 1246
- 97b Chang CL.-T, Chang S.-L, Lee Y.-M, Chiang Y.-M, Chuang D.-Y, Kuo H.-K, Yang W.-C. J. Immunol. 2007; 178: 6984
- 97c Chiang Y.-M, Chang CL.-T, Chang S.-L, Yang W.-C, Shyur L.-F. J. Ethnopharmacol. 2007; 110: 532
- 98 Kumar CR, Tsai C.-H, Chao Y.-S, Lee J.-C. Chem. Eur. J. 2011; 17: 8696
- 99 Chalifoux WA, Ferguson MJ, Tykwinski RR. Eur. J. Org. Chem. 2007; 1001
- 100a Shi Shun AL. K, Tykwinski RR. Angew. Chem. Int. Ed. 2006; 45: 1034; Angew. Chem. 2006, 118, 1050
- 100b Pan Y, Lowary TL, Tykwinski RR. Can. J. Chem. 2009; 87: 1565
- 101 Yang Z, Xie X, Jing P, Zhao G, Zheng J, Zhao C, She X. Org. Biomol. Chem. 2011; 9: 984
- 102a Halbes-Letinois U, Pale P. Tetrahedron Lett. 2002; 43: 2039
- 102b Halbes-Letinois U, Weibel J.-M, Pale P. Chem. Soc. Rev. 2007; 36: 759
- 102c Jiang C, Zhang Z, Xu H, Sun L, Liu L, Wang C. Appl. Organomet. Chem. 2010; 24: 208
- 103a Kuroda I, Musman M, Ohtani I, Ichiba T, Tanaka J, Garcia-Gravalos D, Higa T. J. Nat. Prod. 2002; 65: 1505
- 103b Ledroit V, Debitus C, Lavaud C, Massoit G. Tetrahedron Lett. 2003; 44: 225
- 104a Inuki S, Yoshimitsu Y, Oishi S, Fujii N, Ohno H. Org. Lett. 2009; 11: 4478
- 104b Inuki S, Yoshimitsu Y, Oishi S, Fujii N, Ohno H. J. Org. Chem. 2010; 75: 3831
-
105 Garner P. Tetrahedron Lett. 1984; 25: 5855
- 106 Kito K, Ookura R, Yoshida S, Namikoshi M, Ooi T, Kusumi T. Org. Lett. 2008; 10: 225
- 107 Panarese JD, Walters SP. Org. Lett. 2009; 11: 5086
- 108a Martín MJ, Berrué F, Amade P, Fernandéz R, Francesch A, Reyes F, Cuevas C. J. Nat. Prod. 2005; 68: 1554
- 108b Macías FA, Varela RM, Torres A, Molinillo JM. G. J. Chem. Ecol. 2000; 26: 2173
- 109 Quartieri F, Mesiano LE, Borghi D, Desperati V, Gennari C, Papeo G. Eur. J. Org. Chem. 2011; 6794
- 110a Kobayashi J, Cheng J, Ohta T, Nakamura H, Nozoe S, Hirata Y, Ohizumi Y, Sasaki T. J. Org. Chem. 1988; 53: 6147
- 110b Nozawa K, Tsuda M, Ishiyama H, Sasaki T, Tsuruo T, Kobayashi J. Bioorg. Med. Chem. 2006; 14: 1063
- 111a Kazami S, Muroi M, Kawatani M, Kubota T, Usui T, Kobayashi J, Osada H. Biosci. Biotechnol. Biochem. 2006; 70: 1364
- 111b Schweitzer D, Zhu J, Jarori G, Tanaka J, Higa T, Davisson VJ, Helquist P. Bioorg. Med. Chem. 2007; 15: 3208
- 111c Huss M, Wieczorek H. J. Exp. Biol. 2009; 212: 341
- 111d Beutler JA, McKee TC. Curr. Med. Chem. 2003; 10: 787
- 112 Schweitzer D, Kane J, Strand D, McHenry P, Tenniswood M, Helquist P. Org. Lett. 2007; 9: 4619
- 113 Chen Q, Schweitzer D, Kane J, Davisson VJ, Helquist P. J. Org. Chem. 2011; 76: 5157
- 114 Furstner A, Kattnig E, Lepage O. J. Am. Chem. Soc. 2006; 128: 9194
- 115a Tsuda M, Izui N, Shimbo K, Sato M, Fukushi E, Kawabata J, Katsumata K, Horiguchi T, Kobayashi J. J. Org. Chem. 2003; 68: 5339
- 115b Kang EJ, Lee E. Chem. Rev. 2005; 105: 4348
- 116a Lindquist N, Fenical W, Van Duyne GD, Clardy J. J. Am. Chem. Soc. 1991; 113: 2303
- 116b Fernandez R, Martin MJ, Rodriguez-Acebes R, Reyes F, Francesch A, Cuevas C. Tetrahedron Lett. 2008; 49: 2282
- 117a Li J, Jeong S, Esser L, Harran PG. Angew. Chem. Int. Ed. 2001; 40: 4765
- 117b Li J, Burgett AW. G, Esser L, Amezcua C, Harran PG. Angew. Chem. Int. Ed. 2001; 40: 4770
- 118 Knowles RR, Carpenter J, Blakey SB, Kayano A, Mangion IK, Sinz CJ, MacMillan DW. C. Chem. Sci. 2011; 2: 308
- 119 Booker JE. M, Boto A, Churchill GH, Green CP, Ling M, Meek G, Prabhakaran J, Sincair D, Blake AJ, Pattenden G. Org. Biomol. Chem. 2006; 4: 4193
- 120 Sun X.-Y, Tian X.-Y, Li J.-W, Peng X.-S, Wong HN. C. Chem. Eur. J. 2011; 17: 5874
- 121a Cimino G, De Stefano S, Minale L, Trivellone E. Tetrahedron Lett. 1975; 16: 3727
- 121b Cimino G, De Stefano S, Minale L, Trivellone E. Experientia 1978; 19: 1425
- 122 Marshall JA, Conrow RE. J. Am. Chem. Soc. 1983; 105: 5679
- 123 Ding K, Sun YS, Tian WS. J. Org. Chem. 2011; 76: 1495
- 124 Sun Y.-S, Ding K, Tian Y.-S. Chem. Commun. 2011; 47: 10437
- 125a Akiyama T, Katoh T, Mori K. Angew. Chem. Int. Ed. 2009; 48: 4226
- 125b Christoffers J, Robler U, Werner T. Eur. J. Org. Chem. 2000; 701
- 126a Clayden J, Read B, Hebditch KR. Tetrahedron 2005; 61: 5713
- 126b Zaman GH. L, Arakawa O, Shimosu A, Onoue Y, Nishio S, Nishimura K, Nomoto K, Fujita T. Toxicon 1997; 35: 205
- 127a Lefebvre KA, Robertson A. Toxicon 2010; 56: 218
- 127b Kumar KP, Kumar SP, Nair GA. J. Environ. Biol. 2009; 30: 319
- 127c Vasconcelos V, Azevedo J, Silva M, Ramos V. Mar. Drugs 2010; 8: 59
- 127d Ramsdell JS. Toxins 2010; 2: 1646
- 128 Lemiere G, Sedehizadeh S, Toueg J, Fleary-Roberts N, Clayden J. Chem. Commun. 2011; 47: 3745
- 130 Feng Y, Chen G. Angew. Chem. Int. Ed. 2010; 49: 958
- 132a Kaneko I, Kamoshida K, Takahashi S. J. Antibiot. 1989; 42: 236
- 132b Seto H, Fujioka T, Furihata K, Kaneko I, Takahashi S. Tetrahedron Lett. 1989; 30: 4987
- 133 Momota K, Kaneko I, Kimura S, Mitamura K, Shimada K. Biochem. Biophys. Res. Commun. 1991; 179: 243
- 134 Shimamura H, Breazzano SP, Garfunkle J, Kimball FC, Trzupek JD, Boger DL. J. Am. Chem. Soc. 2010; 132: 7776
- 135a Kummer DA, Brenneman JB, Martin SF. Tetrahedron 2006; 62: 11437
- 135b Huang C, Liu B. Chem. Commun. 2010; 46: 5280
- 135c Kutsumura N, Kiriseko A, Saito T. Tetrahedron Lett. 2012; 53: 3274
- 135d Takao K, Hayakawa N, Yamada R, Yamaguchi T, Saegusa H, Uchida M, Samejima S, Tadano K. J. Org. Chem. 2009; 74: 6452
- 135e Yoshida M, Shoji Y, Shishido K. Org. Lett. 2009; 11: 1441
- 135f Hagiwara H, Suka Y, Nojima T, Hoshi T, Suzuki T. Tetrahedron 2009; 65: 4820
- 136a Hoffmann-Röder A, Krause N. Angew. Chem. Int. Ed. 2004; 43: 1196
- 136b Dembitsky VM, Maoka T. Prog. Lipid Res. 2007; 46: 328
- 136c Brown MJ, Harrison T, Herrinton PM, Hopkins MH, Hutchinson KD, Mishra P, Overman LE. J. Am. Chem. Soc. 1991; 113: 5365
- 136d Brown MJ, Harrison T, Overman LE. J. Am. Chem. Soc. 1991; 113: 5378
- 136e Grese TA, Hutchinson KD, Overman LE. J. Org. Chem. 1993; 58: 2468
- 137 Werness JB, Tang W. Org. Lett. 2011; 13: 3664
- 138 Whitehead A, Mc Reynolds MD, Moore JD, Hanson PR. Org. Lett. 2005; 7: 3375
- 139 Huang SX, Li RT, Liu JP, Lu Y, Chang Y, Lei C, Xiao WL, Yang LB, Zheng QT, Sun HD. Org. Lett. 2007; 9: 2079
- 140 Song WZ, Xiao PG. Chin. Tradit. Herb. Drugs 1982; 13: 40
- 141a Xiao WL, Li RT, Huang SX, Pu JX, Sun HD. Nat. Prod. Rep. 2008; 25: 871
- 141b Sun HD, Qiu SX, Lin LZ, Wang ZY, Lin ZW, Pengsuparp T, Pezzuto JM, Fong H. J. Nat. Prod. 1996; 59: 525
- 142 Xu X.-S, Li Z.-W, Zhang Y.-J, Peng X.-S, Wong HN. C. Chem. Commun. 2012; 48: 8517
- 143a Asakawa Y. Phytochemistry 2004; 65: 623
- 143b Wang L.-N, Zhang J.-Z, Li X, Wang X.-N, Xie C.-F, Zhou J.-C, Lou H.-X. Org. Lett. 2012; 14: 1102
- 144 Hagiwara H, Fukushima M, Kinugawa K, Matsui T, Hoshi T, Suzuki T. Tetrahedron 2011; 67: 4061
- 145a Shibano M, Naito H, Taniguchi M, Wang N.-H, Baba K. Chem. Pharm. Bull. 2006; 54: 717
- 145b Ueda K, Tsujimori M, Kodani S, Chiba A, Kubo M, Masuno K, Sekiya A, Nagai K, Kawagishi H. Bioorg. Med. Chem. 2008; 16: 9467
- 145c Omolo JO, Anke H, Sterner O. Phytochemistry 2002; 60: 431
- 146a Cordes J, Calo F, Anderson K, Pfaffeneder T, Laclef S, White AJ. P, Barrett AG. M. J. Org. Chem. 2012; 77: 652
- 146b Anderson K, Calo F, Pfaffeneder T, White AJ. P, Barrett AG. M. Org. Lett. 2011; 13: 5748
- 147a Hanson JR. Nat. Prod. Rep. 2004; 21: 312
- 147b Katoh T, Akagi T, Noguchi C, Kajimoto T, Node M, Tanaka R, Nishizawa M, Ohtsu H, Suzuki N, Saito K. Bioorg. Med. Chem. 2007; 15: 2736
- 148 Liao X, Stanley LM, Hartwig JF. J. Am. Chem. Soc. 2011; 133: 2088
- 149 Ray D, Ray JK. Org. Lett. 2007; 9: 191
-
150a Castro J, Moyano A, Pericas MA, Riera A, Greene AE, Larena AA, Piniella JF. J. Org. Chem. 1996; 61: 9016
- 150b Srikrishna A, Krishna K, Venkateswarlu S, Kumar P. J. Chem. Soc., Perkin Trans. 1 1995; 2033
- 150c Nakashima H, Sato M, Taniguchi T, Ogasawara K. Tetrahedron Lett. 2000; 41: 2639
-
151a Greene AE, Lansard J.-P, Luche J.-L, Petrier C. J. Org. Chem. 1984; 49: 931
- 151b Takano S, Moriya M, Ogasawara K. Tetrahedron Lett. 1992; 33: 329
- 152 Sipma G, Van der Wal B. Recl. Trav. Chim. Pays-Bas 1968; 87: 715
- 153 Vajs V, Trifunovic S, Janackovic P, Sokovic M, Milosavljevic S, Tesevic V. J. Serb. Chem. Soc. 2004; 69: 969
- 154 Morrison KC, Litz JP, Scherpelz KP, Dossa PD, Vosburg DA. Org. Lett. 2009; 11: 2217
-
155 Katsuki T, Sharpless KB. J. Am. Chem. Soc. 1980; 102: 5974
- 156 Fournier-Nguefack C, Lhoste P, Sinou D. Tetrahedron 1997; 53: 4353
- 157a Zhang Z, Qian H, Longmire J, Zhang X. J. Org. Chem. 2000; 65: 6223
- 157b Raghunath M, Zhang X. Tetrahedron Lett. 2005; 46: 8213
- 158 Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CW, Fong HH, Farnsworth NR, Kinghorn AD, Mehta RG, Moon RC, Pezzuto JM. Science 1997; 275: 218
- 159 Yang Y, Philips D, Pan S. J. Org. Chem. 2011; 76: 1902
- 160 Jeffrey JL, Sarpong R. Tetrahedron Lett. 2009; 50: 1969
- 161 Valenzano DR, Terzibasi E, Genade T, Cattaneo A, Domenici L, Cellerino A. Curr. Biol. 2006; 16: 296
- 162a Nicolaou KC, Sarlah D, Shaw DM. Angew. Chem. Int. Ed. 2007; 46: 4708 ; Angew. Chem. 2007, 119, 4792
- 162b Nicolaou KC, Wu TR, Sarlah D, Shaw DM, Rowcliffe E, Burton DR. J. Am. Chem. Soc. 2008; 130: 11114
- 163 Du C, Li L, Li Y, Xie Z. Angew. Chem. Int. Ed. 2009; 48: 7853
- 164 Eschenmoser A, Schinz H. Helv. Chim. Acta 1954; 37: 881
- 165 Altemoller M, Podlech J, Fenske D. Eur. J. Org. Chem. 2006; 1678
- 166 Harvan DJ, Pero RW. Mycotoxins and other Fungal Related Food Problems, Advances in Chemistry Series. Vol. 149. Rodricks JV. American Chemical Society; Washington (DC, USA): 1976: 344
- 167 Motodate S, Kobayashi T, Fujii M, Mochida T, Kusakabe T, Katoh S, Akita H, Kato K. Chem. Asian J. 2010; 5: 2221
- 168 Li C, Nitka MV, Gloer JB. J. Nat. Prod. 2003; 66: 1302
- 169 Tadd AC, Fielding MR, Willis MC. Chem. Commun. 2009; 6744
- 170a Zhang H, Matsuda H, Kumahara A, Ito Y, Nakamura S, Yoshikawa M. Bioorg. Med. Chem. Lett. 2007; 17: 4972
- 170b Kurume A, Kamata Y, Yamashita M, Wang Q, Matsuda H, Yoshikawa M, Kawasaki I, Ohta S. Chem. Pharm. Bull. 2008; 56: 1264
- 170c Uchiyama M, Ozawa H, Takuma K, Matsumoto Y, Yonehara M, Hiroya K, Sakamoto T. Org. Lett. 2006; 8: 5517
- 171 Rossi R, Carpita A, Bellina F, Stabile P, Mannina L. Tetrahedron 2003; 59: 2067
- 172 Krohn K, Ludewig K, Aust HJ, Draeger S, Schutz B. J. Antibiot. 1994; 47: 113
- 173 Hon Y.-S, Chen H.-F. Tetrahedron Lett. 2007; 48: 8611
- 174 Johnson G, Sunderwirth SG, Gibian H, Coulter AW, Gassner FX. Phytochemistry 1963; 2: 145
- 175 Lin YL, Chang YY, Kuo YH, Shiao MS. J. Nat. Prod. 2002; 65: 745
- 176 Varadaraju TG, Hwu JR. Org. Biomol. Chem. 2012; 10: 5456
- 177 Trost BM, Machacek MR, Tsui HC. J. Am. Chem. Soc. 2005; 127: 7014
- 178 Buckle KA, Kartadarma E. J. Appl. Bacteriol. 1990; 68: 571
- 179a Henderson PJ. F, Lardy HA. J. Biol. Chem. 1970; 245: 1319
- 179b Boulay F, Brandolin G, Lauquin GJ. M, Vignais PV. Anal. Biochem. 1983; 128: 323
- 180a Zamzami N, Susin SA, Marchetti P, Hirsch T, Gomez-Monterrey I, Castedo M, Kroemer G. J. Exp. Med. 1996; 183: 1533
- 181 Français A, Leyva-Pérez A, Etxebarria-Jardi G, Peña J, Ley SV. Chem. Eur. J. 2011; 17: 329
- 182 Kosugi M, Shimizu Y, Migita T. Chem. Lett. 1977; 1423
-
183 Glaser C. Ber. Dtsch. Chem. Ges. 1869; 2: 422
- 184 Onyango EO, Tsurumoto J, Imai N, Takahashi K, Ishihara J, Hatakeyama S. Angew. Chem. Int. Ed. 2007; 46: 6703
- 185 Tietze LF, Stecker F, Zinngrebe J, Sommer KM. Chem. Eur. J. 2006; 12: 8770
- 186a Rochel N, Wurtz JM, Mitschler A, Klaholz B, Moras D. Mol. Cell 2000; 5: 173
- 186b Christakos S, Dhawan P, Benn B, Porta A, Hediger M, Oh GT, Jeung EB, Zhong YAjibade D, Dhawan K, Joshi S. Ann. N. Y. Acad. Sci. 2007; 1116: 340
- 187 Vitamin D . Feldman D, Glorieux FH, Pike V. Elsevier; New York: 2005
- 188 Gogoi P, Sigeiro R, Eduardo S, Mourino A. Chem. Eur. J. 2010; 16: 1432
- 189a Gould SJ. Chem. Rev. 1997; 97: 2499
- 189b He H, Ding WD, Bernan VS, Richardson AD, Ireland CM, Greenstein M, Ellestad GA, Carter GT. J. Am. Chem. Soc. 2001; 123: 5362
- 190a O’Hara KA, Wu X, Patel D, Liang H, Yalowich JC, Chen N, Goodfellow V, Adedayo O, Dmitrienko GI, Hasinoff BB. Free Radical Biol. Med. 2007; 43: 1132
- 190b Ballard TE, Melander C. Tetrahedron Lett. 2008; 49: 3157
- 191a Lei X, Porco JA. Jr. J. Am. Chem. Soc. 2006; 128: 14790
- 191b Nicolaou KC, Li H, Nold AL, Pappo D, Lenzen A. J. Am. Chem. Soc. 2007; 129: 10356
- 191c Kumamoto T, Kitani Y, Tsuchiya H, Yamaguchi K, Seki H, Ishikawa T. Tetrahedron 2007; 63: 5189
- 191d Chen N, Carriere MB, Laufer RS, Taylor NJ, Dmitrienko GI. Org. Lett. 2008; 10: 381
- 192 Woo CM, Lu L, Gholap SL, Smith DR, Herzon SB. J. Am. Chem. Soc. 2010; 132: 2540
- 193 Lu J, Tan X, Chen C. J. Am. Chem. Soc. 2007; 129: 7768
- 194 Asari A, Angelov P, Auty JM, Hayes CJ. Tetrahedron Lett. 2007; 48: 2631
- 195 Trost BM, Horne DB. J, Woltering MJ. Chem. Eur. J. 2006; 12: 6607
- 196 Trost BM, O’Boyle BM. Org. Lett. 2008; 10: 1369
- 197a Judd TC, Williams RM. Angew. Chem. Int. Ed. 2002; 41: 4683
- 197b Judd TC, Williams RM. J. Org. Chem. 2004; 69: 2825
- 198a Paleo MR, Aurrecoechea N, Jung KY, Rapoport H. J. Org. Chem. 2003; 68: 130
- 198b Ducray R, Ciufolini MA. Angew. Chem. Int. Ed. 2002; 41: 4688
- 199 Trost BM, Aponick A. J. Am. Chem. Soc. 2006; 128: 3931
- 200a Woo J, Sigurdsson ST, Hopkins PB. J. Am. Chem. Soc. 1993; 115: 1199
- 200b Paz MM, Hopkins PB. Tetrahedron Lett. 1997; 38: 343
- 201 Jiang M.-Y, Zhang L, Liu R, Dong Z.-J, Liu J.-K. J. Nat. Prod. 2009; 72: 1405
- 202 Hookins DR, Burns AR, Taylor RJ. K. Eur. J. Org. Chem. 2011; 451
- 203 Fletcher AJ, Baxb MN, Willis MC. Chem. Commun. 2007; 4764
- 204a Levy LM, Cabrera GM, Wright JE, Seldes AM. Phytochemistry 2000; 54: 941
- 204b Yamamoto Y, Nishiyama K, Kiriyama N. Chem. Pharm. Bull. 1976; 24: 1853
- 205 Tietze LF, Redert T, Bell HP, Hellkamp S, Levy LM. Chem. Eur. J. 2008; 14: 2527
- 206 The Tetracyclines . Hlavka JJ, Boothe JH. Springer; Berlin: 1985
- 207a Sugimoto K, Yasujima M, Yagihashi S. Curr. Pharm. Des. 2008; 14: 953
- 207b Tsukahara H. Curr. Med. Chem. 2007; 14: 339
- 207c Cho S.-J, Roman G, Yeboah F, Konishi Y. Curr. Med. Chem. 2007; 14: 1653
- 207d Treweek JB, Dickerson TJ, Janda KD. Acc. Chem. Res. 2009; 42: 659
- 207e The Maillard Reaction . Thomas MC, Forbes J. The Royal Society of Chemistry; Cambridge (UK): 2010: 85