An efficient total synthesis of (-)-huperzine A.
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 β-elimination and the accompanying Wagner-Meerwein rearrangement are of particular interest.
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032, China.
Rui
R
Ding
Bing-Feng
BF
Sun
Guo-Qiang
GQ
Lin
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D003500:Cyclization; D000081005:Cyclohexane Monoterpenes; D032502:Lycopodium / Q000737:chemistry; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D012717:Sesquiterpenes; C050426:huperzine A; C039648:pulegone