A Two-Directional Synthesis of (±)-Perhydrohistrionicotoxin

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.

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Journal of organic chemistry 2004-03, Vol.69 (5), p.1598-1602
Hauptverfasser:	Stockman, Robert A, Sinclair, Alex, Arini, Louise G, Szeto, Peter, Hughes, David L
Format:	Artikel
Sprache:	eng
Schlagworte:	Amphibian Venoms - chemical synthesis Amphibian Venoms - chemistry Amphibian Venoms - isolation & purification Animal poisons toxicology. Antivenoms Animals Anura Biological and medical sciences Chemistry Crystallography, X-Ray Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Medical sciences Models, Molecular Molecular Structure Organic chemistry Preparations and properties Skin - chemistry Stereoisomerism Toxicology
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo035639a