Total Synthesis of the Serine/Threonine-Specific Protein Phosphatase Inhibitor Tautomycin1

…, W Liu, AR Chamberlin

Index: Sheppeck II, James E.; Liu, Wen; Chamberlin, A. Richard Journal of Organic Chemistry, 1997 , vol. 62, # 2 p. 387 - 398

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Citation Number: 43

Abstract

A convergent, asymmetric synthesis of the protein phosphatase inhibitor, tautomycin, is described. The natural product was constructed by joining two major fragments of comparable complexity at the C21-C22 bond. Absolute stereochemistry of the C1-C21 ketone originates from (S)-citronellene and (2 R, 3 S)-geraniol epoxide. The anti stereochemical relationships at C6-C7 and C18-C19 were introduced with Duthaler's ...