Chemistry–A European Journal

Platinum??and Gold??Catalyzed Rearrangement Reactions of Propargyl Acetates: Total Syntheses of (−)?螃窿?Cubebene,(−)??Cubebol, Sesquicarene and Related …

A Fürstner, P Hannen

Index: Fuerstner, Alois; Hannen, Peter Chemistry - A European Journal, 2006 , vol. 12, # 11 p. 3006 - 3019

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Citation Number: 203

Abstract

Abstract Propargyl acetates, in the presence of catalytic amounts of late transition-metal salts such as PtCl 2 or AuCl 3, represent synthetic equivalents of α-diazoketones. This notion is corroborated by a concise approach to various sesquiterpene natural products starting from readily available substrates. Specifically,(+)-carvomenthone (17) is converted into propargyl acetate (S)-26 by a sequence involving Stille cross-coupling of its kinetic enol triflate 18, ...