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

作者:Spiccia Nicolas D; Burnley James; Subasinghe Kamani; Perry Christopher; Lefort Laurent; Jackson W Roy; Robinson Andrea J*
来源:Journal of Organic Chemistry, 2017, 82(16): 8725-8732.
DOI:10.1021/acs.joc.7b01257

摘要

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 Bronsted-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.

  • 出版日期2017-8-18