Tetrahedron

Approaches to the DE ring of the polyether antibiotic salinomycin using sharpless asymmetric dihydroxylation

MA Brimble, H Prabaharan

Index: Brimble, Margaret A.; Prabaharan, Hishani Tetrahedron, 1998 , vol. 54, # 10 p. 2113 - 2128

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Citation Number: 17

Abstract

The work described herein provides a model system for appendage of the E ring of epi-17- deoxy-(O-8)-salinomycin3 onto bis-spiroacetal aldehyde 6. The conversion of aldehyde 7 to bicyclic ether 8via silver assisted ring expansion of the mesylate derived from tetrahydrofuran alcohol 33 is described. Attempts to provide a stereoselective synthesis of epoxide 27 required for the preparation of 33 and hence 8 are reported. Alcohol 9 was ...