Tetrahedron p. 3173 - 3188 (1990)
Update date:2022-08-26
Topics:
Zhou, Wei-shan
Jiang, Biao
Pan, Xin-fu
A stereoselective synthesis of the brassinolide side chain involves the lactonization of Z-10 under acidic condition to give an α,β-unsaturated-δ-lactone 11 with the inversion of the configuration at C-22 of the epoxy steroid in quantitative yield.The 22R,23R,24R-γ-hydroxy-δ-lactone 14 was used as key intermediate for the syntheses of brassinolide (1), homobrassinolide (2), and typhasterol (4) as well as the side chain of the dolicholide (3).
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