From Carbamate to Chalcone: Consecutive Anionic Fries Rearrangement, Anionic Si → C Alkyl Rearrangement, and Claisen-Schmidt Condensation

Organic Letters
Singam Naveen KumarRong-Jie Chein

Abstract

A highly efficient one-pot procedure was developed for the synthesis of various 2'-hydroxychalcones from phenyl diethylcarbamate, featuring consecutive Snieckus-Fries rearrangement, anionic Si → C alkyl rearrangement, and Claisen-Schmidt condensation in a single operation. The applicability of this protocol was demonstrated by the highly efficient synthesis of the anti-inflammatory natural product lonchocarpin. The mechanism insight is also provided.

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