Synthesis of 2, 5-dihydrofurans via alkylidene carbene insertion reactions

LF Walker, A Bourghida, S Connolly…

Index: Walker, Louise F.; Bourghida, Ahmed; Connolly, Stephen; Wills, Martin Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 7 p. 965 - 981

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Abstract

The insertion reaction of alkylidene carbenes is demonstrated to be an effective method for the synthesis of 2, 5-dihydrofuran ring systems. The best results have been obtained on substrates containing electron-withdrawing substituents, which appear less prone to the competing rearrangement reaction. This insight has led to the development of a new method for the synthesis of the core structure of the squalestatin–zaragozic acid natural products.