Asymmetric Total Synthesis of a Pentacyclic Lycopodium Alkaloid: Huperzine-Q

被引：80

作者：

Nakayama, Atsushi ^{[1
]}

Kogure, Noriyuki ^{[1
]}

Kitajima, Mariko ^{[1
]}

Takayama, Hiromitsu ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 35期

基金：

日本学术振兴会;

关键词：

alkaloids; natural products; Pauson-Khand reaction; rearrangement; total synthesis; TRANSFER HYDROGENATION; CYCLIZATION; CONVENIENT; REDUCTION; ALCOHOLS;

D O I：

10.1002/anie.201103550

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Right on Q: The first asymmetric total synthesis of (-)-huperzine-Q, which possesses six stereogenic centers and a spiroaminal moiety, has been achieved in 19 steps and 16.4 % overall yield. This synthesis involved a novel stereoselective Pauson-Khand reaction, a vinyl Claisen rearrangement, and a biomimetic spiroaminal formation. TBDPS=tert-butyldiphenylsilyl. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8025 / 8028

页数：4

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