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Synthesis 2021; 53(10): 1683-1705
DOI: 10.1055/a-1379-2312
DOI: 10.1055/a-1379-2312
review
Synthetic Strategies to Access Heteroatomic Spirocentres Embedded in Natural Products
M.P.B. gratefully acknowledges the University of Otago for the provision of a Ph.D. scholarship.
Abstract
The spirocyclic motif is abundant in natural products and provides an ideal three-dimensional template to interact with biological targets. With significant attention historically expended on the synthesis of flat-heterocyclic compound libraries, methods to access the less-explored three-dimensional medicinal-chemical space will continue to increase in demand. Herein, we highlight by reaction class the common strategies used to construct the spirocyclic centres embedded in a series of well-studied natural products.
1 Introduction
2 Cycloadditions
3 Palladium-Catalysed Coupling Reactions
4 Conjugate Additions
5 Imines, Aminals, and Hemiaminal Ethers
6 Mannich-Type Reactions
7 Oxidative Dearomatisation
8 Alkylation
9 Organometallic Additions
10 Conclusions
Key words
spiro compounds - total synthesis - cycloaddition - Michael addition - palladium - natural productsPublikationsverlauf
Eingereicht: 15. Dezember 2020
Angenommen nach Revision: 01. Februar 2021
Accepted Manuscript online:
01. Februar 2021
Artikel online veröffentlicht:
24. Februar 2021
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References
- 1a Li JW.-H, Vederas JC. Science 2009; 325: 161
- 1b Welsch ME, Snyder SA, Stockwell BR. Curr. Opin. Chem. Biol. 2010; 14: 347
- 1c Rodrigues T, Reker D, Schneider P, Schneider G. Nat. Chem. 2016; 8: 531
- 3 Moss G. Pure Appl. Chem. 1999; 71: 531
- 4 Lovering F, Bikker J, Humblet C. J. Med. Chem. 2009; 52: 6752
- 5a Zheng Y, Tice CM, Singh SB. Bioorg. Med. Chem. Lett. 2014; 24: 3673
- 5b Zheng Y.-J, Tice CM. Expert Opin. Drug Discovery 2016; 11: 831
- 5c Claveria-Gimeno R, Vega S, Abian O, Velazquez-Campoy A. Expert Opin. Drug Discovery 2017; 12: 363
- 6 Chupakhin E, Babich O, Prosekov A, Asyakina L, Krasavin M. Molecules 2019; 24: 4165
- 7a Moossavi M, Bagheri B, Scher RK. Dermatol. Clin. 2001; 19: 35
- 7b WHO Model Lists of Essential Medicines (21st List). World Health Organization; Geneva: 2019
- 8a Singh GS, Desta ZY. Chem. Rev. 2012; 112: 6104
- 8b Hong L, Wang R. Adv. Synth. Catal. 2013; 355: 1023
- 8c Carreira EM, Fessard TC. Chem. Rev. 2014; 114: 8257
- 8d Smith LK, Baxendale IR. Org. Biomol. Chem. 2015; 13: 9907
- 8e Gillard RM, Brimble MA. Org. Biomol. Chem. 2019; 17: 8272
- 8f Zhang F.-M, Zhang S.-Y, Tu Y.-Q. Nat. Prod. Rep. 2018; 35: 75
- 9 Diels O, Alder K. Justus Liebigs Ann. Chem. 1928; 460: 98
- 10a Nicolaou KC, Snyder SA, Montagnon T, Vassilikogiannakis G. Angew. Chem. Int. Ed. 2002; 41: 1668
- 10b Hashimoto T, Maruoka K. Chem. Rev. 2015; 115: 5366
- 10c Juhl M, Tanner D. Chem. Soc. Rev. 2009; 38: 2983
- 11a Pellegrini C, Strässler C, Weber M, Borschberg H.-J. Tetrahedron: Asymmetry 1994; 5: 1979
- 11b Palmisano G, Annunziata R, Papeo G, Sisti M. Tetrahedron: Asymmetry 1996; 7: 1
- 11c Fischer C, Meyers C, Carreira EM. Helv. Chim. Acta 2000; 83: 1175
- 11d Cravotto G, Giovenzana GB, Pilati T, Sisti M, Palmisano G. J. Org. Chem. 2001; 66: 8447
- 11e Lizos D, Tripoli R, Murphy JA. Chem. Commun. 2001; 2732
- 11f Selvakumar N, Azhagan AM, Srinivas D, Krishna GG. Tetrahedron Lett. 2002; 43: 9175
- 11g Lizos DE, Murphy JA. Org. Biomol. Chem. 2003; 1: 117
- 11h Chang M.-Y, Pai C.-L, Kung Y.-H. Tetrahedron Lett. 2005; 46: 8463
- 11i Murphy JA, Tripoli R, Khan TA, Mali UW. Org. Lett. 2005; 7: 3287
- 11j Trost BM, Brennan MK. Org. Lett. 2006; 8: 2027
- 11k Jaegli S, Vors J.-P, Neuville L, Zhu J. Synlett 2009; 2997
- 11l Deppermann N, Thomanek H, Prenzel AH. G. P, Maison W. J. Org. Chem. 2010; 75: 5994
- 11m Kulkarni MG, Dhondge AP, Chavhan SW, Borhade AS, Shaikh YB, Birhade DR, Desai MP, Dhatrak NR. Beilstein J. Org. Chem. 2010; 6: 876
- 11n Thomson JE, Kyle AF, Ling KB, Smith SR, Slawin AM. Z, Smith AD. Tetrahedron 2010; 66: 3801
- 11o White JD, Li Y, Ihle DC. J. Org. Chem. 2010; 75: 3569
- 11p Hong S, Jung M, Park Y, Ha MW, Park C, Lee M, Park H.-g. Chem. Eur. J. 2013; 19: 9599
- 11q Mukaiyama T, Ogata K, Sato I, Hayashi Y. Chem. Eur. J. 2014; 20: 13583
- 11r Kim M, Kim G. Bull. Korean Chem. Soc. 2012; 33: 1821
- 11s Lakshmaiah G, Kawabata T, Shang M, Fuji K. J. Org. Chem. 1999; 64: 1699
- 11t Jossang A, Jossang P, Hadi HA, Sevenet T, Bodo B. J. Org. Chem. 1991; 56: 6527
- 12a Anderton N, Cockrum PA, Colegate SM, Edgar JA, Flower K, Vit I, Willing RI. Phytochemistry 1998; 48: 437
- 12b Colegate S, Anderton N, Edgar J, Bourke C, Oram R. Aust. Vet. J. 1999; 77: 537
- 13 Whitesell JK, Chen HH, Lawrence RM. J. Org. Chem. 1985; 50: 4663
- 14 Li C, Chan C, Heimann AC, Danishefsky SJ. Angew. Chem. Int. Ed. 2007; 46: 1444
- 15a Badart MP, Squires CM. L, Baird SK, Hawkins BC. Tetrahedron Lett. 2016; 57: 5108
- 15b Shaala LA, Youssef DT, Sulaiman M, Behery FA, Foudah AI, Sayed KA. E. Mar. Drugs 2012; 10: 2492
- 15c Compagnone RS, Avila R, Suárez AI, Abrams OV, Rangel HR, Arvelo F, Piña IC, Merentes E. J. Nat. Prod. 1999; 62: 1443
- 15d Kobayashi J. i, Tsuda M, Agemi K, Shigemori H, Ishibashi M, Sasaki T, Mikami Y. Tetrahedron 1991; 47: 6617
- 15e Acosta AL, Rodríguez AD. J. Nat. Prod. 1992; 55: 1007
- 15f Copp BR, Ireland CM, Barrows LR. J. Nat. Prod. 1992; 55: 822
- 15g Perry NB, Blunt JW, McCombs JD, Munro MH. G. J. Org. Chem. 1986; 51: 5476
- 16 Gunasekera SP, Cross SS. J. Nat. Prod. 1992; 55: 509
- 17a Nakamura Y, Kobayashi M, Nakamura H, Wu H, Kobayashi J. i, Ohizumi Y. Eur. J. Biochem. 1987; 167: 1
- 17b Nakamura H, Wu H, Kobayashi J. i, Nakamura Y, Ohizumi Y, Hirata Y. Tetrahedron Lett. 1985; 26: 4517
- 18 Buchanan MS, Carroll AR, Wessling D, Jobling M, Avery VM, Davis RA, Feng Y, Hooper JN. A, Quinn RJ. J. Nat. Prod. 2009; 72: 973
- 19a Zhu G, Yang F, Balachandran R, Höök P, Vallee RB, Curran DP, Day BW. J. Med. Chem. 2006; 49: 2063
- 19b Rodríguez AD, Piña IC. J. Nat. Prod. 1993; 56: 907
- 19c Gunasekera M, Gunasekera SP. J. Nat. Prod. 1989; 52: 753
- 19d Kobayashi J. i, Honma K, Sasaki T, Tsuda M. Chem. Pharm. Bull. 1995; 43: 403
- 19e Gopichand Y, Schmitz FJ. Tetrahedron Lett. 1979; 20: 3921
- 19f Das P, Hamme AT. II. Eur. J. Org. Chem. 2015; 5159
- 19g Kita Y, Tohma H, Inagaki M, Hatanaka K, Yakura T. J. Am. Chem. Soc. 1992; 114: 2175
- 19h Ogamino T, Obata R, Tomoda H, Nishiyama S. Bull. Chem. Soc. Jpn. 2006; 79: 134
- 19i Ogamino T, Nishiyama S. Tetrahedron Lett. 2005; 46: 1083
- 19j Ogamino T, Ishikawa Y, Nishiyama S. Heterocycles 2003; 61: 73
- 20 Iwagawa T, Miyazaki M, Okamura H, Nakatani M, Doe M, Takemura K. Tetrahedron Lett. 2003; 44: 2533
- 21 Dai J, Jiménez JI, Kelly M, Williams PG. J. Org. Chem. 2010; 75: 2399
- 22a Skiredj A, Beniddir MA, Joseph D, Leblanc K, Bernadat G, Evanno L, Poupon E. Angew. Chem. Int. Ed. 2014; 53: 6419
- 22b Skiredj A, Beniddir MA, Joseph D, Leblanc K, Bernadat G, Evanno L, Poupon E. Org. Lett. 2014; 16: 4980
- 23 Duchemin N, Skiredj A, Mansot J, Leblanc K, Vasseur J.-J, Beniddir MA, Evanno L, Poupon E, Smietana M, Arseniyadis S. Angew. Chem. Int. Ed. 2018; 57: 11786
- 24 Ma S.-G, Gao R.-M, Li Y.-H, Jiang J.-D, Gong N.-B, Li L, Lü Y, Tang W.-Z, Liu Y.-B, Qu J, Lü H.-N, Li Y, Yu S.-S. Org. Lett. 2013; 15: 4450
- 25a Wei L, Xiao M, Xie Z. Org. Lett. 2014; 16: 2784
- 25b Zhao N, Ren X, Ren J, Lü H, Ma S, Gao R, Li Y, Xu S, Li L, Yu S. Org. Lett. 2015; 17: 3118
- 25c Song L, Yao H, Tong R. Org. Lett. 2014; 16: 3740
- 26 Barrow CJ, Sun HH. J. Nat. Prod. 1994; 57: 471
- 27a Hart DJ. ARKIVOC 2010; (iv): 32
- 27b Larsen TO, Frydenvang K, Frisvad JC, Christophersen C. J. Nat. Prod. 1998; 61: 1154
- 27c Ariza MR, Larsen TO, Petersen BO, Duus J. Ø, Christophersen C, Barrero AF. J. Nat. Prod. 2001; 64: 1590
- 27d Larsen TO, Petersen BO, Duus J. Ø, Sørensen D, Frisvad JC, Hansen ME. J. Nat. Prod. 2005; 68: 871
- 27e Koyama N, Inoue Y, Sekine M, Hayakawa Y, Homma H, Omura S, Tomoda H. Org. Lett. 2008; 10: 5273
- 27f Proença Barros FA, Rodrigues-Filho E. Biochem. Syst. Ecol. 2005; 33: 257
- 28 Wu M, Ma D. Angew. Chem. Int. Ed. 2013; 52: 9759
- 29a Kende AS, Fan J, Chen Z. Org. Lett. 2003; 5: 3205
- 29b Chen Z, Fan J, Kende AS. J. Org. Chem. 2004; 69: 79
- 30a Ding K, Lu Y, Nikolovska-Coleska Z, Qiu S, Ding Y, Gao W, Stuckey J, Krajewski K, Roller PP, Tomita Y, Parrish DA, Deschamps JR, Wang S. J. Am. Chem. Soc. 2005; 127: 10130
- 30b Lo MM. C, Neumann CS, Nagayama S, Perlstein EO, Schreiber SL. J. Am. Chem. Soc. 2004; 126: 16077
- 30c Antonchick AP, Gerding-Reimers C, Catarinella M, Schürmann M, Preut H, Ziegler S, Rauh D, Waldmann H. Nat. Chem. 2010; 2: 735
- 30d Antonchick AP, Schuster H, Bruss H, Schürmann M, Preut H, Rauh D, Waldmann H. Tetrahedron 2011; 67: 10195
- 31 von Nussbaum F, Danishefsky SJ. Angew. Chem. Int. Ed. 2000; 39: 2175
- 32a Edmondson S, Danishefsky SJ, Sepp-Lorenzino L, Rosen N. J. Am. Chem. Soc. 1999; 121: 2147
- 32b Wang H, Ganesan A. J. Org. Chem. 2000; 65: 4685
- 32c Edmondson SD, Danishefsky SJ. Angew. Chem. Int. Ed. 1998; 37: 1138
- 32d Overman LE, Rosen MD. Angew. Chem. Int. Ed. 2000; 39: 4596 ; Angew. Chem., 2000, 112, 4768
- 33a Miyake FY, Yakushijin K, Horne DA. Angew. Chem. Int. Ed. 2004; 43: 5357
- 33b Miyake FY, Yakushijin K, Horne DA. Org. Lett. 2004; 6: 4249
- 34a Kitahara K, Shimokawa J, Fukuyama T. Chem. Sci. 2014; 5: 904
- 34b Overman LE, Rosen MD. Tetrahedron 2010; 66: 6514
- 35a Onishi T, Sebahar PR, Williams RM. Org. Lett. 2003; 5: 3135
- 35b Onishi T, Sebahar PR, Williams RM. Tetrahedron 2004; 60: 9503
- 35c Sebahar PR, Osada H, Usui T, Williams RM. Tetrahedron 2002; 58: 6311
- 35d Sebahar PR, Williams RM. J. Am. Chem. Soc. 2000; 122: 5666
- 36a Marti C, Carreira EM. J. Am. Chem. Soc. 2005; 127: 11505
- 36b Meyers C, Carreira EM. Angew. Chem. Int. Ed. 2003; 42: 694
- 37 Bagul TD, Lakshmaiah G, Kawabata T, Fuji K. Org. Lett. 2002; 4: 249
- 38 Trost BM, Stiles DT. Org. Lett. 2007; 9: 2763
- 39 Encarnación RD, Sandoval E, Malmstrøm J, Christophersen C. J. Nat. Prod. 2000; 63: 874
- 40 Bardhan S, Schmitt DC, Porco JA. Org. Lett. 2006; 8: 927
- 41 Kikuchi H, Miyagawa Y, Sahashi Y, Inatomi S, Haganuma A, Nakahata N, Oshima Y. J. Org. Chem. 2004; 69: 352
- 42a Dai M, Krauss IJ, Danishefsky SJ. J. Org. Chem. 2008; 73: 9576
- 42b Dai M, Danishefsky SJ. J. Am. Chem. Soc. 2007; 129: 3498
- 43a Gerwick WH, Fenical W. J. Org. Chem. 1981; 46: 22
- 43b Gerwick WH, Fenical W, Fritsch N, Clardy J. Tetrahedron Lett. 1979; 20: 145
- 43c O’Brien ET, Asai DJ, Jacobs RS, Wilson L. Mol. Pharmacol. 1989; 35: 635
- 43d White SJ, Jacobs RS. Mol. Pharmacol. 1983; 24: 500
- 44 Mori K, Komatsu M. Liebigs Ann. Chem. 1988; 1988: 107
- 45 Mori K, Koga Y. Bioorg. Med. Chem. Lett. 1992; 2: 391
- 46 Xing X, Demuth M. Synlett 1999; 987
- 47a Wolfe JP, Jack Li J. An Introduction to Palladium Catalysis . In Palladium in Heterocyclic Chemistry, A Guide for the Synthetic Chemist . Li JJ, Gribble GW. Tetrahedron Organic Chemistry Series, Vol. 26, Chap. 1; Elsevier; Amsterdam: 2007: 1-35
- 47b Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
-
47c The Nobel Prize in Chemistry 2010 (Nobel Media AB 2021; accessed Feb 16, 2021), see: https://www.nobelprize.org/prizes/chemistry/2010/advanced-information
- 48 Heck RF. Palladium-Catalyzed Vinylation of Organic Halides . In Organic Reactions, Vol. 27. Dauben WG. John Wiley & Sons; New York: 1982: 345-390
- 49 Zhang W, Liu Z, Li S, Yang T, Zhang Q, Ma L, Tian X, Zhang H, Huang C, Zhang S, Ju J, Shen Y, Zhang C. Org. Lett. 2012; 14: 3364
- 50 Blair LM, Sperry J. Chem. Commun. 2016; 52: 800
- 51a Saxton JE. Alkaloids of Gelsemium Species . In The Alkaloids: Chemistry and Physiology, Chap. 6, Vol. 8. Manske RH. F. Academic Press; New York: 1965: 93-117
- 51b Liu Z.-J, Lu R.-R. Gelsemium Alkaloids . In The Alkaloids: Chemistry and Pharmacology, Chap. 2, Vol. 33. Brossi A. Academic Press; San Diego: 1988: 83-140
- 51c Takayama H, Sakai S.-i. Recent Advances in the Chemistry of Gelsemium Alkaloids. In Studies in Natural Products Chemistry, Part C, Vol. 15. Atta-ur-Rahman Elsevier; Amsterdam: 1995: 465-518
- 52a Shimokawa J, Harada T, Yokoshima S, Fukuyama T. J. Am. Chem. Soc. 2011; 133: 17634
- 52b Harada T, Shimokawa J, Fukuyama T. Org. Lett. 2016; 18: 4622
- 52c Newcomb ET, Knutson PC, Pedersen BA, Ferreira EM. J. Am. Chem. Soc. 2016; 138: 108
- 52d Baldwin SW, Doll RJ. Tetrahedron Lett. 1979; 20: 3275
- 52e Hamer NK. J. Chem. Soc., Chem. Commun. 1990; 102
- 52f Kende AS, Luzzio MJ, Mendoza JS. J. Org. Chem. 1990; 55: 918
- 52g Phisalaphong C, Takayama H, Sakai S.-i. Tetrahedron Lett. 1993; 34: 4035
- 52h Takayama H, Odaka H, Aimi N, Sakai S.-i. Tetrahedron Lett. 1990; 31: 5483
- 52i Takayama H, Kitajima M, Ogata K, Sakai S. J. Org. Chem. 1992; 57: 4583
- 52j Takayama H, Tominaga Y, Kitajima M, Aimi N, Sakai S. J. Org. Chem. 1994; 59: 4381
- 52k Kitajima M, Takayama H, Sakai S.-i. J. Chem. Soc., Perkin Trans. 1 1994; 1573
- 52l Kogure N, Ishii N, Kitajima M, Wongseripipatana S, Takayama H. Org. Lett. 2006; 8: 3085
- 52m Yamada Y, Kitajima M, Kogure N, Wongseripipatana S, Takayama H. Tetrahedron Lett. 2009; 50: 3341
- 52n Yamada Y, Kitajima M, Kogure N, Takayama H. Tetrahedron 2008; 64: 7690
- 52o Yamada Y, Kitajima M, Kogure N, Wongseripipatana S, Takayama H. Chem. Asian J. 2011; 6: 166
- 52p Beyersbergen van Henegouwen WG, Fieseler RM, Rutjes FP. J. T, Hiemstra H. Angew. Chem. Int. Ed. 1999; 38: 2214
- 52q Beyersbergen van Henegouwen WG, Fieseler RM, Rutjes FP. J. T, Hiemstra H. J. Org. Chem. 2000; 65: 8317
- 52r Shimokawa J, Harada T, Yokoshima S, Fukuyama T. Pure Appl. Chem. 2012; 84: 1643
- 52s Diethelm S, Carreira EM. J. Am. Chem. Soc. 2015; 137: 6084
- 52t Diethelm S, Carreira EM. J. Am. Chem. Soc. 2013; 135: 8500
- 53a Schwarz H, Marion L. Can. J. Chem. 1953; 31: 958
- 53b Jin H.-L, Xu R.-S. Acta Chim. Sinica 1982; 40: 1129
- 53c Wenkert E, Orr JC, Garratt S, Hansen JH, Wickberg B, Leicht CL. J. Org. Chem. 1962; 27: 4123
- 53d Przybylska M, Marion L. Can. J. Chem. 1961; 39: 2124
- 54 Madin A, O’Donnell CJ, Oh T, Old DW, Overman LE, Sharp MJ. J. Am. Chem. Soc. 2005; 127: 18054
- 55 Lin L.-Z, Cordell GA, Ni C.-Z, Clardy J. Phytochemistry 1991; 30: 1311
- 56a Polonsky J, Merrien M.-A, Prangé T, Pascard C, Moreau S. J. Chem. Soc., Chem. Commun. 1980; 601
- 56b Prangé T, Billion M.-A, Vuilhorgne M, Pascard C, Polonsky J, Moreau S. Tetrahedron Lett. 1981; 22: 1977
- 56c Yamazaki M, Okuyama E, Kobayashi M, Inoue H. Tetrahedron Lett. 1981; 22: 135
- 56d Lee BH, Clothier MF, Dutton FE, Nelson SJ, Johnson SS, Thompson DP, Geary TG, Whaley HD, Haber CL, Marshall VP, Kornis GI, McNally PL, Ciadella JI, Martin DG, Bowman JW, Baker CA, Coscarelli EM, Alexander-Bowman SJ, Davis JP, Zinser EW, Wiley V, Lipton MF, Mauragis MA. Curr. Top. Med. Chem. 2002; 2: 779
- 57a Wiley V, Cialdella J, Yurek D, Whaley H, Marshall V. J. Antibiot. 1996; 49: 1006
- 57b Sommer K, Williams RM. Tetrahedron 2009; 65: 3246
- 57c Williams RM, Cox RJ. Acc. Chem. Res. 2003; 36: 127
- 57d Williams RM, Stocking EM, Sanz-Cervera JF. Biosynthesis of Prenylated Alkaloids Derived from Tryptophan . In Biosynthesis: Aromatic Polyketides, Isoprenoids, Alkaloids . Leeper FJ, Vederas JC. Springer-Verlag; Berlin: 2000: 97-173
- 58 Trost BM, Cramer N, Bernsmann H. J. Am. Chem. Soc. 2007; 129: 3086
- 59 Trost BM, Bringley DA, Zhang T, Cramer N. J. Am. Chem. Soc. 2013; 135: 16720
- 60a Macías FA, Galindo JL. G, Varela RM, Torres A, Molinillo JM. G, Fronczek FR. Org. Lett. 2006; 8: 4513
- 60b Macías FA, Varela RM, Torres A, Molinillo JG. Tetrahedron Lett. 1998; 39: 427
- 61a Norcott P, McErlean CS. P. Eur. J. Org. Chem. 2014; 5056
- 61b Norcott P, McErlean CS. P. Aust. J. Chem. 2018; 71: 366
- 61c Miyawaki A, Kikuchi D, Niki M, Manabe Y, Kanematsu M, Yokoe H, Yoshida M, Shishido K. J. Org. Chem. 2012; 77: 8231
- 61d Huang C, Zhang W, Liu B. Sci. China Chem. 2011; 54: 43
- 61e Miyawaki A, Manabe Y, Yoshida M, Shishido K. Tetrahedron Lett. 2012; 53: 1236
- 61f Yang L, Feng J, Li J, Liu B. Tetrahedron Lett. 2015; 56: 4931
- 61g Bai W.-J, Green JC, Pettus TR. R. J. Org. Chem. 2012; 77: 379
- 62a Rapson WS. J. Chem. Soc. 1938; 282
- 62b Murray AW. Nature 1962; 196: 484
- 62c Perold GW, Pachler KG. R. J. Chem. Soc. C 1966; 1918
- 62d Perold GW, Carlton L, Howard AS, Michael JP. J. Chem. Soc., Perkin Trans. 1 1988; 881
- 63 Li X.-L, Cheng X, Yang L.-M, Wang R.-R, Zheng Y.-T, Xiao W.-L, Zhao Y, Xu G, Lu Y, Chang Y, Zheng Q.-T, Zhao Q.-S, Sun H.-D. Org. Lett. 2006; 8: 1937
- 64 Poss AJ, Belter RK. Tetrahedron Lett. 1987; 28: 2555
- 65 Wang Z, Zhao K, Fu J, Zhang J, Yin W, Tang Y. Org. Biomol. Chem. 2013; 11: 2093
- 66a Le Goff R, Lawson AM, Daïch A, Comesse S. Org. Biomol. Chem. 2013; 11: 1818
- 66b Görmen M, Le Goff R, Lawson AM, Daïch A, Comesse S. Tetrahedron Lett. 2013; 54: 2174
- 67a Chou T, Kuramoto M, Otani Y, Shikano M, Yazawa K, Uemura D. Tetrahedron Lett. 1996; 37: 3871
- 67b Clive DL. J, Yu M, Wang J, Yeh VS. C, Kang S. Chem. Rev. 2005; 105: 4483
- 68a Tsubosaka Y, Murata T, Kinoshita K, Yamada K, Uemura D, Hori M, Ozaki H. Eur. J. Pharmacol. 2010; 628: 128
- 68b Kuramoto M, Tong C, Yamada K, Chiba T, Hayashi Y, Uemura D. Tetrahedron Lett. 1996; 37: 3867
- 69 Wu H, Zhang H, Zhao G. Tetrahedron 2007; 63: 6454
- 70a Xu S, Unabara D, Uemura D, Arimoto H. Chem. Asian J. 2014; 9: 367
- 70b Xu S, Arimoto H, Uemura D. Angew. Chem. Int. Ed. 2007; 46: 5746
- 71 Christie HS, Heathcock CH. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 12079
- 72 Sugiyama R, Nishimura S, Ozaki T, Asamizu S, Onaka H, Kakeya H. Angew. Chem. Int. Ed. 2016; 55: 10278
- 73 Twiner MJ, Rehmann N, Hess P, Doucette GJ. Mar. Drugs 2008; 6: 39
- 74 Satake M, Ofuji K, Naoki H, James KJ, Furey A, McMahon T, Silke J, Yasumoto T. J. Am. Chem. Soc. 1998; 120: 9967
- 75 Furey A, Moroney C, Magdalena AB, Fidalgo Saez MJ, Lehane M, James KJ. Environ. Sci. Technol. 2003; 37: 3078
- 76a Jauffrais T, Marcaillou C, Herrenknecht C, Truquet P, Séchet V, Nicolau E, Tillmann U, Hess P. Toxicon 2012; 60: 582
- 76b Salas R, Tillmann U, John U, Kilcoyne J, Burson A, Cantwell C, Hess P, Jauffrais T, Silke J. Harmful Algae 2011; 10: 774
- 77 Nicolaou KC, Pihko PM, Diedrichs N, Zou N, Bernal F. Angew. Chem. Int. Ed. 2001; 40: 1262
- 78a Nicolaou KC, Koftis TV, Vyskocil S, Petrovic G, Tang W, Frederick MO, Chen DY. K, Li Y, Ling T, Yamada YM. A. J. Am. Chem. Soc. 2006; 128: 2859
- 78b Nicolaou KC, Chen DY. K, Li Y, Uesaka N, Petrovic G, Koftis TV, Bernal F, Frederick MO, Govindasamy M, Ling T, Pihko PM, Tang W, Vyskocil S. J. Am. Chem. Soc. 2006; 128: 2258
- 78c Nicolaou K, Pihko PM, Bernal F, Frederick MO, Qian W, Uesaka N, Diedrichs N, Hinrichs J, Koftis TV, Loizidou E. J. Am. Chem. Soc. 2006; 128: 2244
- 78d Nicolaou K, Frederick MO, Petrovic G, Cole KP, Loizidou EZ. Angew. Chem. Int. Ed. 2006; 45: 2609
- 78e Nicolaou K, Frederick MO, Loizidou EZ, Petrovic G, Cole KP, Koftis TV, Yamada YM. Chem. Asian J. 2006; 1: 245
- 79a Evans DA, Kværnø L, Mulder JA, Raymer B, Dunn TB, Beauchemin A, Olhava EJ, Juhl M, Kagechika K. Angew. Chem. Int. Ed. 2007; 46: 4693
- 79b Evans DA, Dunn TB, Kværnø L, Beauchemin A, Raymer B, Olhava EJ, Mulder JA, Juhl M, Kagechika K, Favor DA. Angew. Chem. Int. Ed. 2007; 46: 4698
- 79c Evans DA, Kværnø L, Dunn TB, Beauchemin A, Raymer B, Mulder JA, Olhava EJ, Juhl M, Kagechika K, Favor DA. J. Am. Chem. Soc. 2008; 130: 16295
- 80a Kenton NT, Adu-Ampratwum D, Okumu AA, Zhang Z, Chen Y, Nguyen S, Xu J, Ding Y, McCarron P, Kilcoyne J, Rise F, Wilkins AL, Miles CO, Forsyth CJ. Angew. Chem. Int. Ed. 2018; 57: 805
- 80b Kenton NT, Adu-Ampratwum D, Okumu AA, McCarron P, Kilcoyne J, Rise F, Wilkins AL, Miles CO, Forsyth CJ. Angew. Chem. Int. Ed. 2018; 57: 810
- 81a Wanyonyi AW, Chhabra SC, Mkoji G, Eilert U, Njue WM. Phytochemistry 2002; 59: 79
- 81b Mahato SB, Sahu NP, Ganguly AN, Kasai R, Tanaka O. Phytochemistry 1980; 19: 2017
- 81c Al Chami L, Méndez R, Chataing B, O’Callaghan J, Usubillaga A, LaCruz L. Phytother. Res. 2003; 17: 254
- 81d Ghosh M, Sinhababu SP, Sukul NC, Sahu NP, Mahato SB. Int. J. Pharmacogn. 1994; 32: 184
- 82 Kalalinia F, Karimi-Sani I. Phytother. Res. 2017; 31: 858
- 83a Wei G, Wang J, Du Y. Bioorg. Med. Chem. Lett. 2011; 21: 2930
- 83b Wei G, Wei D, Du Y. Sci. China Chem. 2012; 55: 1247
- 84 Nonato MG, Garson MJ, Truscott RJ, Carver JA. Phytochemistry 1993; 34: 1159
- 85 Seah KY, Macnaughton SJ, Dallimore JW. P, Robertson J. Org. Lett. 2014; 16: 884
- 86a Blicke FF. The Mannich Reaction . In Organic Reactions, Vol. 1. Adams R. John Wiley & Sons; New York: 1942: 303-341
- 86b Mannich C, Krösche W. Arch. Pharm. 1912; 250: 647
- 87 Greger H. Phytochem. Rev. 2019; 18: 463
- 88a Liu X.-Y, Wang F.-P. Nat. Prod. Commun. 2015; 10: 1093
- 88b Williams DR, Brown DL, Benbow JW. J. Am. Chem. Soc. 1989; 111: 1923
- 88c Martin SF, Barr KJ. J. Am. Chem. Soc. 1996; 118: 3299
- 88d Martin SF, Barr KJ, Smith DW, Bur SK. J. Am. Chem. Soc. 1999; 121: 6990
- 88e Noro T, Fukushima S, Ueno A, Miyase T, Iitaka Y, Saiki Y. Chem. Pharm. Bull. 1979; 27: 1495
- 88f Fu J, Shen H, Chang Y, Li C, Gong J, Yang Z. Chem. Eur. J. 2014; 20: 12881
- 88g Sakata K, Aoki K, Chang C.-F, Sakurai A, Tamura S, Murakoshi S. Agric. Biol. Chem. 1978; 42: 457
- 88h Hu J.-P, Yang D.-H, Lin W.-H, Cai S.-Q. Helv. Chim. Acta 2009; 92: 2125
- 88i Hitotsuyanagi Y, Fukaya H, Takeda E, Matsuda S, Saishu Y, Zhu S, Komatsu K, Takeya K. Tetrahedron 2013; 69: 6297
- 88j Xu R.-S. Some Bioactive Natural Products from Chinese Medicinal Plants. In Studies in Natural Products Chemistry, Part B, Vol. 21. Atta-ur-Rahman Elsevier; Amsterdam: 2000: 729-772
- 88k Hitotsuyanagi Y, Takeda E, Fukaya H, Takeya K. Tetrahedron Lett. 2008; 49: 7376
- 88l Taniguchi T, Tanabe G, Muraoka O, Ishibashi H. Org. Lett. 2008; 10: 197
- 88m Iizuka H, Irie H, Masaki N, Osaki K, Uyeo S. J. Chem. Soc., Chem. Commun. 1973; 125
- 88n Kende AS, Martin Hernando JI, Milbank JB. J. Org. Lett. 2001; 3: 2505
- 88o Kende AS, Martin Hernando JI, Milbank JB. J. Tetrahedron 2002; 58: 61
- 88p Ye Y, Qin G.-W, Xu R.-S. J. Nat. Prod. 1994; 57: 665
- 89a Nozoye T. Chem. Pharm. Bull. 1958; 6: 309
- 89b Nozoye T, Shibanuma Y, Shigehisa A. Yakugaku Zasshi 1975; 95: 758
- 89c Haginiwa J, Sakai S.-I, Aimi N, Yamanaka E, Shinma N. Yakugaku Zasshi 1973; 93: 448
- 89d Houghton PJ, Shellard EJ. Planta Med. 1974; 26: 104
- 89e Nozoye T. Chem. Pharm. Bull. 1958; 6: 309
- 89f Bindra JS. Oxindole Alkaloids . In The Alkaloids: Chemistry and Physiology, Vol. 14, Chap. 2. Manske RH. F. Academic Press; New York: 1973: 83-121
- 90 Wanner MJ, Ingemann S, van Maarseveen JH, Hiemstra H. Eur. J. Org. Chem. 2013; 1100
- 91 Roche SP, Porco JA. Jr. Angew. Chem. Int. Ed. 2011; 50: 4068
- 92a Baker Dockrey SA, Lukowski AL, Becker MR, Narayan AR. H. Nat. Chem. 2018; 10: 119
- 92b Jackson SK, Wu KL, Pettus TR. R. Sequential Reactions Initiated by Oxidative Dearomatization. Biomimicry or Artifact? In Biomimetic Organic Synthesis. Poupon E, Nay B. Wiley-VCH; Weinheim: 2011: 723-749
- 93a Heilmann J, Mayr S, Brun R, Rali T, Sticher O. Helv. Chim. Acta 2000; 83: 2939
- 93b Heilmann J, Brun R, Mayr S, Rali T, Sticher O. Phytochemistry 2001; 57: 1281
- 93c Salim AA, Su B.-N, Chai H.-B, Riswan S, Kardin LB. S, Ruskandi A, Farnsworth NR, Swanson SM, Kinghorn AD. Tetrahedron Lett. 2007; 48: 1849
- 93d Chin Y.-W, Salim AA, Su B.-N, Mi Q, Chai H.-B, Riswan S, Kardono LB. S, Ruskandi A, Farnsworth NR, Swanson SM, Kinghorn AD. J. Nat. Prod. 2008; 71: 390
- 94 Song L, Yao H, Dai Y, Wu M, Tong R. Tetrahedron Lett. 2016; 57: 4257 ; and references cited therein
- 95 Wong YS. Chem. Commun. 2002; 686
- 96 Ralifo P, Crews P. J. Org. Chem. 2004; 69: 9025
- 97 White KN, Amagata T, Oliver AG, Tenney K, Wenzel PJ, Crews P. J. Org. Chem. 2008; 73: 8719
- 98a Lamb RA, Aberle NS, Lucas NT, Lessene G, Hawkins BC. Angew. Chem. Int. Ed. 2017; 56: 14663
- 98b Lamb RA, Lucas NT, Lessene G, Hawkins BC. J. Org. Chem. 2018; 83: 10120
- 99 Buchanan MS, Carroll AR, Wessling D, Jobling M, Avery VM, Davis RA, Feng Y, Xue Y, Öster L, Fex T, Deinum J, Hooper JN. A, Quinn RJ. J. Med. Chem. 2008; 51: 3583
- 100 Li Y.-X, Cheng C, Tang L, Yang Y.-Y. Org. Biomol. Chem. 2020; 18: 4551
- 101a Pflieger P, Mioskowski C, Salaun JP, Weissbart D, Durst F. Tetrahedron Lett. 1989; 30: 2791
- 101b Falck J, Chandrasekhar S, Manna S, Chiu CC. S, Mioskowski C, Wetzel I. J. Am. Chem. Soc. 1993; 115: 11606
- 102 Hanson FR, Eble TE. J. Bacteriol. 1949; 58: 527
- 103a Molina J.-M, Tourneur M, Sarfati C, Chevret S, de Gouvello A, Gobert J.-G, Balkan S, Derouin F. New Engl. J. Med. 2002; 346: 1963
- 103b Killough JH, Magill GB, Smith RC. Science 1952; 115: 71
- 104a Ingber D, Fujita T, Kishimoto S, Sudo K, Kanamaru T, Brem H, Folkman J. Nature 1990; 348: 555
- 104b Kwon J.-Y, Jeong H.-W, Kim H.-K, Kang K.-H, Chang Y.-H, Bae K.-S, Choi J.-D, Lee U.-C, Son K.-H, Kwon B.-M. J. Antibiot. 2000; 53: 799
- 105 Corey EJ, Snider BB. J. Am. Chem. Soc. 1972; 94: 2549
- 106a Kim D, Ahn SK, Bae H, Choi WJ, Kim HS. Tetrahedron Lett. 1997; 38: 4437
- 106b Vosburg DA, Weiler S, Sorensen EJ. Angew. Chem. Int. Ed. 1999; 38: 971
- 106c Hutchings M, Moffat D, Simpkins NS. Synlett 2001; 661
- 106d Taber DF, Christos TE. J. Am. Chem. Soc. 1999; 121: 5589
- 106e Boiteau J.-G, Van de Weghe P, Eustache J. Org. Lett. 2001; 3: 2737
- 106f Bedel O, Haudrechy A, Langlois Y. Eur. J. Org. Chem. 2004; 3813
- 106g Yamaguchi J, Toyoshima M, Shoji M, Kakeya H, Osada H, Hayashi Y. Angew. Chem. Int. Ed. 2006; 45: 789
- 106h Yamaguchi J, Hayashi Y. Chem. Eur. J. 2010; 16: 3884
- 106i Takahashi S, Hongo Y, Ye YQ, Koshino H. Tetrahedron: Asymmetry 2011; 22: 703
- 107 Nakamura R, Ishibashi K. J. Agric. Chem. Soc. Jpn. 1958; 32: 739
- 108 Nozoe S, Morisaki M, Tsuda K, Iitaka Y, Takahashi N, Tamura S, Ishibashi K, Shirasaka M. J. Am. Chem. Soc. 1965; 87: 4968
- 109a Leung PC, Taylor WA, Wang JH, Tipton CL. J. Biol. Chem. 1984; 259: 2742
- 109b Fujiwara H, Matsunaga K, Kumagai H, Ishizuka M, Ohizumi Y. Pharm. Pharmacol. Commun. 2000; 6: 427
- 109c Shen X, Krasnoff SB, Lu S.-W, Dunbar CD, O’Neal J, Turgeon BG, Yoder OC, Gibson DM, Hamann MT. J. Nat. Prod. 1999; 62: 895
- 109d Au TK, Chick WS. H, Leung PC. Life Sci. 2000; 67: 733
- 110a Noguchi N, Nakada M. Org. Lett. 2006; 8: 2039
- 110b Tsuna K, Noguchi N, Nakada M. Chem. Eur. J. 2013; 19: 5476
- 110c Tsuna K, Noguchi N, Nakada M. Angew. Chem. Int. Ed. 2011; 50: 9452