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
收藏
页码：4446 / 4449
页数：4
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