Facile entry to substituted decahydroquinoline alkaloids. Total synthesis of lepadins A-E and H | |
Pu XT(蒲晓涛) ; Ma DW(马大为) | |
刊名 | J. Org. Chem. |
2006 | |
卷号 | 71期号:17页码:6562-6572 |
ISSN号 | 0022-3263 |
其他题名 | 十氢喹啉生物碱的有效合成方法;lepadins A-E and H的全合成 |
通讯作者 | 马大为 |
英文摘要 | Condensation 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. |
学科主题 | 生命有机化学 |
收录类别 | SCI |
原文出处 | http://dx.doi.org/10.1021/jo061070c |
语种 | 英语 |
WOS记录号 | WOS:000239685200035 |
公开日期 | 2013-02-19 |
内容类型 | 期刊论文 |
源URL | [http://202.127.28.38/handle/331003/15515] |
专题 | 上海有机化学研究所_生命有机化学国家重点实验室 |
推荐引用方式 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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