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A Two-Directional Synthesis of (±)-Perhydrohistrionicotoxin

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School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, NR4 7TJ, UK, and GlaxoSmithKline, Gunnels Wood Road, Stevenage, Herts, SG1 2NY, UK
Cite this: J. Org. Chem. 2004, 69, 5, 1598–1602
Publication Date (Web):February 6, 2004
https://doi.org/10.1021/jo035639a
Copyright © 2004 American Chemical Society

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    Abstract

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    An entirely two-directional synthesis of (±)-perhydrohistrionicotoxin is presented, utilizing a tandem oxime formation/Michael addition/[3 + 2] cycloaddition as the key step. This approach also constitutes formal syntheses of (±)-histrionicotoxin and (±)-histrionicotoxin 235A.

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     School of Chemical Sciences and Pharmacy, University of East Anglia.

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     X-ray Crystallographic Unit, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, UK.

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    X-ray crystal data for compounds 5 and 14. This material is available free of charge via the Internet at http://pubs.acs.org.

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