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Report | Regular issue | Vol 20, No. 8, 1983, pp.1567-1576
Published online, 1st January, 1970
DOI: 10.3987/R-1983-08-1567
Synthesis of 9-Hexadecen-5-olides; Hypothetical Intermediates in the Biosynthesis of Brefeldin A

Tomihisa Ohta, Masayuki Sunagawa, Kazuko Nishimaki, and Shigeo Nozoe

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Four types of lactones 1-4 which might be biosynthetic intermediates of brefeldin A have been synthesized. In the course of their synthesis, it was found that coupling of a hydroxy phosphonium salt and a carbomethoxy-aldehyde gave a macrocyclic lactone in onepot probably by a sequential reaction in which intramolecular Wittig condensation followed transesterification.