☆ 4.8 Article

Enantioselective Modular Synthesis of Cyclohexenones: Total Syntheses of (+)-Crypto- and (+)-Infectocaryone

ORGANIC LETTERS (2010)

Journal

ORGANIC LETTERS

Volume 12, Issue 17, Pages 3886-3889

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/ol101588j

Keywords

-

Categories

Chemistry, Organic

Funding

Deutsche Forschungsgemeinschaft [SFB 623]
Fonds der Chemischen Industrie

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Abstract

A modular synthesis of cyclohexenones is described and applied to the first enantioselective total syntheses of (+)-crypto- and (+)-infectocaryone. Key steps in the synthesis of cyclohexenones are an iridium-catalyzed allylic alkylation, nucleophilic allylation, and ring-closing metathesis. On the way to (+)-cryptocaryone, a catch and release strategy involving an iodolactonization/elimination and a regioselective C-acylation were used.

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