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

doi:10.1021/acs.joc.7b01257

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

School of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

5 Citations (Scopus)

Abstract

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 language	English
Pages (from-to)	8725-8732
Number of pages	8
Journal	The Journal of Organic Chemistry
Volume	82
Issue number	16
DOIs	https://doi.org/10.1021/acs.joc.7b01257
Publication status	Published - 18 Aug 2017

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10.1021/acs.joc.7b01257

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abstract = "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 Br{\o}nsted-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.",

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AU - Burnley, James

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AU - Perry, Christopher

AU - Lefort, Laurent

AU - Jackson, W. Roy

AU - Robinson, Andrea J.

PY - 2017/8/18

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AB - 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.

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IS - 16

ER -

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

Abstract

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New metal catalysed tandem routes to nitrogen containing compounds

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

Abstract

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New metal catalysed tandem routes to nitrogen containing compounds

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