Stereocontrolled Synthesis of Multisubstituted 1,3-Dienes via an Allene–Claisen Rearrangement

Abstract

We herein developed a stereoselective synthetic method for the preparation of multisubstituted 1,3-dienes via an allene–Claisen rearrangement. The Claisen rearrangement of anti-allenyl alcohols provided (1E,3Z)-1,3-dienes, which are essential components of bongkrekic acid, in high stereoselectivities. To demonstrate the synthetic utility of the resulting 1,3-dienes, further functional transformations and Diels–Alder reactions are described.

Key words

allenes - Claisen rearrangement - conjugated dienes - bongkrekic acid - stereoselectivity

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