An Efficient Total Synthesis of (-)-Huperzine A

被引：50

作者：

Ding, Rui ^{[1
]}

Sun, Bing-Feng ^{[1
]}

Lin, Guo-Qiang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, CAS Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 17期

基金：

中国国家自然科学基金;

关键词：

HUPERZINE-A; ENANTIOSELECTIVE SYNTHESIS; FORMAL SYNTHESIS; CORE STRUCTURE; ALKALOIDS; ROUTE; ACETYLCHOLINESTERASE; CYCLIZATION; ANNULATION; ARYLATION;

D O I：

10.1021/ol301951r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of Lycopodium alkaloid (-)-huperzine A has been accomplished in 10 steps with 17% overall yield from commercially abundant (R)-pulegone. The synthetic route features an efficient synthesis of 4 via a Buchwald-Hartwig coupling reaction, a dianion-mediated highly stereoselective alkylation of 4, and a rare example of an intramolecular Heck reaction of an enamine-type substrate. The stereoselective beta-elimination and the accompanying Wagner-Meerwein rearrangement are of particular interest.

引用

页码：4446 / 4449

页数：4

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