A Formal Synthesis of (-)-Perhydrohistrionicotoxin Using a Cross Metathesis-Hydrogenation Approach

Nicolas D. Spiccia, James Burnley, Kamani Subasinghe, Christopher Perry, Laurent Lefort, W. Roy Jackson, Andrea J. Robinson

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The development of an efficient, high yielding six-step convergent synthesis of the semisynthetic alkaloid (-)-perhydrohistrionicotoxin is described. The key transformations include the cross metathesis of a Brønsted-acid masked primary homoallylic amine with a vinyl cyclohexenone and a regioselective palladium catalyzed hydrogenation. This sequence generated the advanced Winterfeldt spirocyclic precursor in 47% overall yield, with a longest linear sequence of five steps.

Original languageEnglish
Pages (from-to)8725-8732
Number of pages8
JournalThe Journal of Organic Chemistry
Issue number16
Publication statusPublished - 18 Aug 2017

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