A two-directional synthesis of (±)-perhydrohistrionicotoxin

Robert A. Stockman; Alex Sinclair; Louise G. Arini; Peter Szeto; David L. Hughes

doi:10.1021/jo035639a

A two-directional synthesis of (±)-perhydrohistrionicotoxin

Robert A. Stockman, Alex Sinclair, Louise G. Arini, Peter Szeto, David L. Hughes

School of Chemistry

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

45 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1598-1602
Number of pages	5
Journal	The Journal of Organic Chemistry
Volume	69
Issue number	5
Early online date	6 Feb 2004
DOIs	https://doi.org/10.1021/jo035639a
Publication status	Published - 1 Mar 2004

Access to Document

10.1021/jo035639a

http://pubs.acs.org/doi/abs/10.1021/jo035639a

Cite this

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title = "A two-directional synthesis of (±)-perhydrohistrionicotoxin",

abstract = "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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T1 - A two-directional synthesis of (±)-perhydrohistrionicotoxin

AU - Stockman, Robert A.

AU - Sinclair, Alex

AU - Arini, Louise G.

AU - Szeto, Peter

AU - Hughes, David L.

PY - 2004/3/1

Y1 - 2004/3/1

N2 - 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.

AB - 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.

U2 - 10.1021/jo035639a

DO - 10.1021/jo035639a

M3 - Article

VL - 69

SP - 1598

EP - 1602

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 5

ER -