The Journal of Organic Chemistry

Macrocyclic lactone formation through sulfide contraction. Synthesis of (.+-.)-diplodialide A

RE Ireland, FR Brown Jr

Index: Ireland, Robert E.; Brown, Frank R. Journal of Organic Chemistry, 1980 , vol. 45, # 10 p. 1868 - 1880

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Citation Number: 74

Abstract

A methodology for the synthesis of macrocyclic@-keto lactones from w-hydroxy thioamides is described. The hydroxy thioamides were esterified with chloroacetyl chloride, and the resulting chloro esters underwent Eschenmoser sulfide contraction when treated with sodium iodide, diisopropylethylamine, and triethyl phosphite in acetonitrile. The@-keto lactones were obtained in 25-58% yield. The utility of the method was demonstrated by ...