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Tordanone, un stéroïde replié avec une jonction de cycle A/B β‐ cis (5β) et B/C α‐ cis (8α)
Author(s) -
Haag Thierry,
Hetru Charles,
Luu Bang
Publication year - 1989
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.19890720817
Subject(s) - chemistry , stereochemistry , steric effects , ring (chemistry) , stereospecificity , steroid , bent molecular geometry , catalysis , biochemistry , organic chemistry , hormone
Tordanone, a Twice Bent Steroid Structure with Ring A/B β‐cis (5β)‐ and Ring B/C α‐ cis (8α)‐Fused The 3β, 14α, 25‐trihydroxy‐5β, 8α‐cholestan‐6‐one ( = tordanone; 4 ) has been prepared by stereospecific hydrogenation of 3β, 14α, 25‐trihydroxy‐5β‐cholesta‐7,22ξ‐dien‐6‐one ( 5 ). This is the first stereospecific synthesis of a B/C cis ‐fused steroid belonging to the 5β, 8α ‐cholestane group with a H‐atom at positions 5β (A/B cis ‐fused) and 8α. The resulting twice bent structure shows a particularly strong steric hindrance of the β‐face where CH 3 (18) at the C/D ring junction and H β C(7) of the B ring are very close to each other. Structural features and mechanistic aspects of the hydrogenation are discussed.