Total synthesis of (±)-aspidophylline A.

作者: Weiwu Ren , Qian Wang , Jieping Zhu

DOI: 10.1002/ANIE.201310929

关键词:

摘要: A total synthesis of aspidophylline A, a pentacyclic akuammiline-type monoterpene indole alkaloid, is described. The features: 1) rapid access to fully functionalized dihydrocarbazole through the desymmetrization readily available 2-allyl-2-(o-nitrophenyl)cyclohexane-1,3-dione; 2) an intramolecular azidoalkoxylation an enecarbamate install both furoindoline ring and azido functionality; 3) an Michael addition for construction 2-azabicyclo[3.3.1]nonane system.

参考文章(62)
Uffe Anthoni, Carsten Christophersen, Per Halfdan Nielsen, Naturally Occurring Cyclotryptophans and Cyclotryptamines Alkaloids: Chemical and Biological Perspectives. ,vol. 13, pp. 163- 236 ,(1999) , 10.1016/S0735-8210(99)80025-9
Daniel Solé, Josep Bonjoch, Silvina García-Rubio, Emma Peidró, Joan Bosch, Totalsynthese von (−)‐Strychnin über den Wieland‐Gumlich‐Aldehyd Angewandte Chemie. ,vol. 111, pp. 408- 410 ,(1999) , 10.1002/(SICI)1521-3757(19990201)111:3<408::AID-ANGE408>3.0.CO;2-Q
M.-Lluïsa Bennasar, Ester Zulaica, Manel López, Joan Bosch, Studies on the synthesis of akuammiline-type alkaloids. Construction of the hexahydro-1,5-methanoazocino[3,4-b]indole fragment Tetrahedron Letters. ,vol. 29, pp. 2361- 2364 ,(1988) , 10.1016/S0040-4039(00)86060-8
Michael C Willis, Christelle K Claverie, The selective preparation and Suzuki coupling reactivity of cyclic 1,3-dione derived mono- and ditriflates Tetrahedron Letters. ,vol. 42, pp. 5105- 5107 ,(2001) , 10.1016/S0040-4039(01)00933-9
Tsugunori Watanabe, Naoki Umezawa, Nobuki Kato, Tsunehiko Higuchi, Synthesis of the Carbon Framework of Scholarisine A by Intramolecular Oxidative Coupling Chemistry - A European Journal. ,vol. 19, pp. 4255- 4261 ,(2013) , 10.1002/CHEM.201203454
Yuan Mi, Jürg V. Schreiber, E. J. Corey, Total synthesis of (+)-α-onocerin in four steps via four-component coupling and tetracyclization steps Journal of the American Chemical Society. ,vol. 124, pp. 11290- 11291 ,(2002) , 10.1021/JA027373F
Kyoko Nozaki, Koichiro Oshima, Kiichiro Uchimoto, Et3B-induced radical addition of R3SnH to acetylenes and its application to cyclization reaction Journal of the American Chemical Society. ,vol. 109, pp. 2547- 2549 ,(1987) , 10.1021/JA00242A068
Yoshizumi Yasui, Tomoyo Kinugawa, Yoshiji Takemoto, Synthetic studies on vincorine: access to the 3a,8a-dialkyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole skeleton Chemical Communications. pp. 4275- 4277 ,(2009) , 10.1039/B907210A
Gregory L. Adams, Patrick J. Carroll, Amos B. Smith, Total Synthesis of (+)-Scholarisine A Journal of the American Chemical Society. ,vol. 134, pp. 4037- 4040 ,(2012) , 10.1021/JA211840K