Journal of Organic Chemistry p. 5439 - 5444 (1994)
Update date:2022-08-04
Topics:
Kocovsky, Pavel
Baines, Richard S.
Estrone (8b) has been synthesized in four steps from 3β-acetoxy-19-hydroxyandrost-5-en-17-one (2b), readily available from an industrial precursor.A key feature of the strategy is a stereoelectronically controlled, Tl(III)-mediated degradation (2b -> 5b).Oppenauer oxidation of diol 6b, resulting from saponification of the acetate 5b, afforded the unsaturated 10β-hydroxy ketone 7b, acid treatment of which induced aromatization affording 8b.An alternative route including dehydration (5b -> 9b) followed by Oppenauer oxidation (10b -> 8b) gave comparable results.This strategy has first been developed with the aid of cholestane model compounds (2a -> 5a) and then successfully applied to the synthesis of analogues in the cholestane, androstane, and pregnane series to produce the corresponding 19-nor-10β-hydroxy derivatives 7a-d and A-aromatic steroids 8a-d.
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