A novel synthesis of brassinolide and related compounds

Z Wei-Shan, B Jiang, X Pan

Index: Wei-Shan, Zhou; Jiang, Biao; Pan, Xin-fu Journal of the Chemical Society, Chemical Communications, 1989 ,  # 10  p. 612 - 613

Full Text: HTML

Citation Number: 8

Abstract

A stereoselective synthesis of the natural promoting steroids, brassinolide, homobrassinolide, and typhasterol is described, which involves construction of a side chain by lactonisation of Z-(5) under acidic conditions to give an α, β-unsaturated δ-lactone (6) with the inversion of the configuration at C-22 of the epoxy steroid in quantitative yield.