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

John T. Dixon; Fanie R. Van Heerden; Cedric W. Holzapfel

doi:10.1016/j.tetasy.2004.11.028

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

John T. Dixon, Fanie R. Van Heerden, Cedric W. Holzapfel

Chemical Sciences

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

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 formation under acidic conditions.

Original language	English
Pages (from-to)	393-401
Number of pages	9
Journal	Tetrahedron Asymmetry
Volume	16
Issue number	2
DOIs	https://doi.org/10.1016/j.tetasy.2004.11.028
Publication status	Published - 24 Jan 2005

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/j.tetasy.2004.11.028

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abstract = "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 formation under acidic conditions.",

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AB - 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 formation under acidic conditions.

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

Abstract

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