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Review | Special issue | Vol 64, No. 1, 2004, pp.605-658
Published online, 26th October, 2004
DOI: 10.3987/REV-04-SR(P)3
β-Lactones as Intermediates for Natural Product Total Synthesis and New Transformations

Yingcai Wang, Reginald L. Tennyson, Daniel Romo*

*Department of Chemistry, Texas A & M University, College Station, Texas 77843-3255, U.S.A.

Abstract

The exploration of β-lactone reactivity and transformations has continued since the first synthesis of these strained heterocycles by Einhorn in 1883. The principal reactivity modes of β-lactones include nucleophilic addition resulting in either acyl C2-O1 or alkyl C4-O1 cleavage, rearrangement leading to ring expansion, decarboxylation, and electrophilic reactions of β-lactone enolates. Recent advances in asymmetric β-lactone synthesis has led to further developments in the area of novel transformations of β-lactones and significantly increased applications in natural product total synthesis. The latter topic is the focus of this review and covers the period inclusive to the end of 2003.