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A Concise Total Synthesis of dl -Histrionicotoxin

2006; American Chemical Society; Volume: 128; Issue: 39 Linguagem: Inglês

10.1021/ja065015x

1943-2984

Maheswaran S. Karatholuvhu, Alex Sinclair, Annabella F. Newton, Marie‐Lyne Alcaraz, Robert A. Stockman, P. L. Fuchs,

Marine Toxins and Detection Methods

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.