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■ Palladium(II)-catalyzed Stereocontrolled Cyclization via Hemiacetal Intermediates: Total Synthesis of 5-Epi-prelactone C

Masahiro Miyazawa, Magsarjav Narantsetseg, Hajime Yokoyama, Seiji Yamaguchi, and Yoshiro Hirai*

*Department of Chemistry, Faculty of Science, Toyama University, Gofuku 3190, Toyama 930, Japan

Abstract

Palladium(II)-catalyzed cyclization of 3,7-dihydroxy-4-methyl-5-octenal derivative was carried out to give 2,3,4,6-tetrasubstituted tetrahydropyran with stereoselective 1,3-chirality transfer in net retention of stereochemistry. The cyclized product was converted into 5-epi-prelactone C.