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23 May 08:20

Total Synthesis of (±)-Waihoensene

by Hee-Yoon Lee, Hongsoo Lee, Taek Kang

Abstract

The first total synthesis of waihoensene, a tetracyclic diterpene containing an angular triquinane and a six-membered ring, with four contiguous quaternary carbon atoms, was achieved through the tandem cycloaddition reaction of an allenyl diazo substrate containing a six-membered ring via trimethylenemethane (TMM) diyl intermediate.

Thumbnail image of graphical abstract

Taking a shortcurt: The total synthesis of waihoensene, a tetracyclic diterpene natural product with four contiguous quaternary carbon centers was achieved. Key step is a tandem cycloaddition reaction of an allenyl diazo substrate via a trimethylenemethane intermediate.