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Paper | Special issue | Vol 52, No. 3, 2000, pp.1241-1249
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S138
Development of a Method for the Synthesis of α-Substituted α,β-Unsaturated Lactones Based on Stille-Type Pd-catalyzed Carbonylation of (Z)-ω-Iodoalkenols. An Efficient and Selective Synthesis of (+)-Hamabiwa-lactone B

Baiqiao Liao and Ei-ichi Negishi*

*Herbert C. Brown Laboratory of Chemistry, Purdue University, West Lafayette, Indiana 47907, U.S.A.

Abstract

Pd-Catalyzed carbonylative lactonization of (Z)-ω-iodoalkenols can be applied to synthesize α,β-unsaturated lactones containing an alkenyl or alkynyl substituent in the α position, providing a generally superior alternative to recently developed methods involving Pd-catalyzed α-substitution of α-stannyl esters, as exemplified by a highly expeditious synthesis of (+)-hamabiwalactone B.