A New Synthetic Route to (±)‐Perhydrohistrionicotoxin
- 2 November 1977
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 60 (7) , 2294-2302
- https://doi.org/10.1002/hlca.19770600720
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.This publication has 14 references indexed in Scilit:
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