5 years ago

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

A Formal Synthesis of (−)-Perhydrohistrionicotoxin Using a Cross Metathesis–Hydrogenation Approach
W. Roy Jackson, Nicolas D. Spiccia, Andrea J. Robinson, Christopher Perry, Laurent Lefort, Kamani Subasinghe, James Burnley
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01257

DOI: 10.1021/acs.joc.7b01257

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