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Facile entry to substituted decahydroquinoline alkaloids. Total synthesis of lepadins A-E and H
Alternative Title十氢喹啉生物碱的有效合成方法;lepadins A-E and H的全合成
Pu XT(蒲晓涛); Ma DW(马大为)
2006
Source PublicationJ. Org. Chem.
ISSN0022-3263
Volume71Issue:17Pages:6562-6572
AbstractCondensation of a L-alanine derived delta-bromo-beta-silyloxy-propylamine with 1,3-cyclohexadione followed by alkylative cyclization produces a bicyclic enone. Diastereoselective Pt/C-catalyzed hydrogenation of this enone in HOAc provides a 5-oxo-cis-fused decahydroquinoline. Wittig olefination of this decahydroquinoline and subsequent epimerization of the resulting 5-formyl intermediate gives rise to a 5-beta-formyl decahydroquinoline exclusively. In a parallel procedure, Peterson reaction of this decahydroquinoline and subsequent hydrogenation of the generated 5-exo-olefin provides a decahydroquinoline with a 5-alpha-substituent predominantly. For these two diastereoselective processes, using the intermediates without N-protection as the substrates is essential because the corresponding N-Boc intermediates give poor diastereoselectivity. The intermediate with beta-form side chain is further converted into lepadins A-C via carbon chain elongation, while the intermediate with alpha-form side chain is transformed into lepadins D, E, and H and corresponding 5'-epimers via connection with two sulfones generated from two Sharpless epoxidation products. By comparison of the rotations and NMR data, the stereochemistry of lepadins D, E, and H is assigned as 2S, 3R, 4aS, 5S, 8aR, 5'R.
Subject Area生命有机化学
Department上海有机所
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Indexed BySCI
Language英语
WOS IDWOS:000239685200035
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Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/15515
Collection生命有机化学国家重点实验室
Corresponding AuthorMa DW(马大为)
Recommended Citation
GB/T 7714
Pu XT,Ma DW. Facile entry to substituted decahydroquinoline alkaloids. Total synthesis of lepadins A-E and H[J]. J. Org. Chem.,2006,71(17):6562-6572.
APA 蒲晓涛,&马大为.(2006).Facile entry to substituted decahydroquinoline alkaloids. Total synthesis of lepadins A-E and H.J. Org. Chem.,71(17),6562-6572.
MLA 蒲晓涛,et al."Facile entry to substituted decahydroquinoline alkaloids. Total synthesis of lepadins A-E and H".J. Org. Chem. 71.17(2006):6562-6572.
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