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Synthese der 2,5‐Diole des A‐nor‐5α‐Cholestans und A‐nor‐5β‐Cholestans
Author(s) -
Heckendorn R.,
Tamm Ch.
Publication year - 1967
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19670500730
Subject(s) - cholestane , chemistry , diol , hydrogen peroxide , medicinal chemistry , stereochemistry , organic chemistry
Abstract Treatment of A‐nor‐Δ 3(5) ‐cholestene‐2‐one ( 1 ) with alkaline hydrogen peroxide gave 3β,5‐epoxy‐A‐nor‐cholestane‐2‐one ( 2 ) and the epoxylactone 3 (B AEYER ‐V ILLIGER reaction). LiAlH 4 ‐reduction of 2 yielded A‐nor‐5β‐cholestane‐2β,5‐diol( 4 ) (main product) and A‐nor‐5β‐cholestane‐2α,5‐diol ( 5 ). LiAlH 4 ‐reduction of 1 led mainly to A‐nor‐Δ 3(5) ‐cholestene‐2α‐ol ( 8 ). Catalytic hydrogenation of 8 gave the known A‐nor‐5α‐cholestane‐2α‐01 ( 10 ), A‐nor‐5β‐cholestane‐2α‐01 ( 11 ) (main product), A‐nor‐5β‐cholestane ( 9 ) and A‐nor‐5β‐cholestane‐2‐one ( 12 ). By LiAlH 4 ‐reduction of the ketones 12 and 13 the two additional alcohols 14 and 15 were obtained.