Tetrahedron

Stereoselective total synthesis of 1α, 25S, 26-trihydroxycholecalciferol

PM Wovkulich, F Barcelos, AD Batcho, JF Sereno…

Index: Wovkulich; Barcelos; Batcho; et al. Tetrahedron, 1984 ,  vol. 40,  # 12  p. 2283 - 2296

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Citation Number: 68

Abstract

A total synthesis of 1α, 25S, 26-trihydroxycholecalciferol (2) has been accomplished via an efficient convergent approach. The remote chiral center at C-25 was introduced by a regiospecific and diastereoselective 1, 3-dipolar cycloaddition of the C-23 nitrone 27 with methyl methacrylate. Subsequent transformation of the resulting isoxazolidine led to the key synthon 3, which on coupling to the anion 4 and deprotection produced the metabolite 2.