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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 124, Issue 49, Pages 14655-14662Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja0279646
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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.
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