A Concise Total Synthesis of dl-Histrionicotoxin

A Concise Total Synthesis of dl-Histrionicotoxin

The synthesis of (±)-histrionicotoxin has been achieved in just nine steps using a two-directional synthesis strategy. Key reactions include a two-directional cross-metathesis, a tandem oxime formation/Michael addition/1,4-prototopic shift/[3 + 2]-cycloaddition cascade, a selective Z,Z-bisenyne form...

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Veröffentlicht in:Journal of the American Chemical Society 2006-10, Vol.128 (39), p.12656-12657
Hauptverfasser: Karatholuvhu, Maheswaran S, Sinclair, Alex, Newton, Annabella F, Alcaraz, Marie-Lyne, Stockman, Robert A, Fuchs, Philip L
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Amphibian Venoms - chemical synthesis
Amphibian Venoms - chemistry
Animals
Anura
Chemistry
Exact sciences and technology
General and physical chemistry
Stereoisomerism
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Beschreibung
Zusammenfassung:The synthesis of (±)-histrionicotoxin has been achieved in just nine steps using a two-directional synthesis strategy. Key reactions include a two-directional cross-metathesis, a tandem oxime formation/Michael addition/1,4-prototopic shift/[3 + 2]-cycloaddition cascade, a selective Z,Z-bisenyne formation, and a one-pot N−O and bischloroacetylene reduction.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja065015x