Tetrahedron: Asymmetry

Preparation of an analogue of orbicuside A, an unusual cardiac glycoside

JT Dixon, FR van Heerden, CW Holzapfel

文献索引：Dixon, John T.; Van Heerden, Fanie R.; Holzapfel, Cedric W. Tetrahedron Asymmetry, 2005 , vol. 16, # 2 p. 393 - 401

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被引用次数: 16

摘要

A steroid containing a multi-linked glycoside, analogous to the bufadienolide orbicuside A, has been prepared. The key steps were (i) the preparation of a 2α-allyloxycarbonyloxy-3β- hydroxy steroid,(ii) a Ferrier reaction between the steroid and a rhamnal derivative,(iii) removal of protecting group and oxidation of the 2-hydroxy group,(iv) dihydroxylation of the pseudoglycal from the sterically more hindered side and finally (v) ring closure by acetal ...