ABSTRACT
[reaction: see text] Possible structures of feigrisolide C were synthesized via ring-closing olefin metathesis reaction of a diester derivative prepared from 8-epi-nonactic acid, but physical characteristics of the synthetic samples did not match with those of the natural sample of feigrisolide C.
Subject(s)
Lactones/chemistry , Lactones/chemical synthesis , Cyclization , Molecular Structure , Stereoisomerism , Streptomyces griseus/chemistryABSTRACT
A macrodiolide antibiotic pamamycin-607 was synthesized by joining two hydroxy acid components. Three cis-2, 5-disubstituted tetrahydrofuran rings in the molecule were stereoselectively prepared by radical cyclization reactions of beta-alkoxyvinyl ketone intermediates and a beta-alkoxymethacrylate substrate. The key step of the synthesis is characterized by the predominant threo product formation in the radical cyclization reaction of a beta-alkoxymethacrylate intermediate.
