A concise total synthesis of DL-histrionicotoxin.

Maheswaran S Karatholuvhu, Alex Sinclair, Annabella F Newton, Marie-Lyne Alcaraz, Robert A Stockman, Philip L Fuchs

Index: J. Am. Chem. Soc. 128 , 12656, (2006)

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Abstract

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.