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A New Synthetic Route to (±)-Perhydrohistrionicotoxin

✍ Scribed by E. J. Corey; Martin Petrzilka; Yoichiro Ueda

Publisher
John Wiley and Sons
Year
1977
Tongue
German
Weight
604 KB
Volume
60
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Starting from ethyl 2‐cyclohexen‐1‐carboxylate (3) the total synthesis of the perhydrohistrionicotoxin intermediate 23 was achieved in 25% overall‐yield. The two key steps involve a positionally specific addition of HOBr to the oxime‐olefin 7 and the alkylation of bromooxime 17 with 1‐lithio‐1‐butyne. The latter represents a novel method for stereospecific and position‐specific introduction of a nucleophilic butyl equivalent in α‐position to a ketonic carbonyl group.

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