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An Efficient Total Synthesis of (−)-Huperzine A

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journal contribution
posted on 2012-09-07, 00:00 authored by Rui Ding, Bing-Feng Sun, Guo-Qiang Lin
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.