(1 5.11.96) Rearrangement of 5a -and 5j3-cholesta-6,8(14)-dienes (13a and 13b, resp.) in the presence of anhydrous toluene-4-sulfonic acid in acetic acid leads to 5a-and @-12(13 -+ 14)-abeo-cholesta-8,13(17)-dienes (15s and 15b, resp.) via 5a-and S,!l-cholesta-8,14-dienes (14a and 14b, resp.), respectively. Epimerization at C(20) of the spirosteradienes 15a and 15b occurs with increasing reaction time. Molecular-mechanics calculation of the relative stabilities of these compounds and of congeners thereof is in agreement with the observed reaction pathway.

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