Tandem Transacylation/Debenzylation of β-Lactones Mediated by FeCl3 Leading to γ- and δ-Lactones: Application to the Synthesis of (-)-Grandinolide

Ronald Zemribo; M. Scott Champ; Daniel Romo

doi:10.1055/s-1996-5391

Synlett 1996; 1996(3): 278-280
DOI: 10.1055/s-1996-5391

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Tandem Transacylation/Debenzylation of β-Lactones Mediated by FeCl₃ Leading to γ- and δ-Lactones: Application to the Synthesis of (-)-Grandinolide

Ronald Zemribo, M. Scott Champ, Daniel Romo^*

^*Department of Chemistry, Texas A&M University, College Station, Texas 77843-3255, USA, Fax (409) 845-4719; Internet romo@chemvx.tamu.edu

Abstract

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The one step conversion of β-lactones bearing a pendant benzyloxy group to γ- and δ-lactones via a transacylation/debenzylation process is effected using FeCl₃. This procedure in conjunction with a previously reported diastereoselective [2+2] cycloaddition has been applied to an asymmetric synthesis of (-)-grandinolide.

β-lactone - debenzylation - transacylation - ferric chloride - grandinolide

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