Preparation of an analogue of orbicuside A, an unusual cardiac glycoside
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.
Dixon, John T.,Van Heerden, Fanie R.,Holzapfel, Cedric W.
p. 393 - 401
(2007/10/03)
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