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A new route to steroid ring C aromatization from readily available precursors
Author(s) -
Anastasia Mario,
Allevi Pietro,
Fiecchi Alberto,
Scala Antonio
Publication year - 1982
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02535108
Subject(s) - aromatization , epimer , chemistry , steroid , p toluenesulfonic acid , organic chemistry , ring (chemistry) , hydrochloric acid , stereochemistry , medicinal chemistry , catalysis , biochemistry , hormone
3β‐Acetoxy‐8α,9α‐epoxy‐5α‐cholest‐14‐ene ( 1 ); 3β‐acetoxy‐14α,15α‐epoxy‐5α‐cholest‐8‐ene ( 2 ); 3β‐acetoxy‐5α‐cholest‐8(14)‐ene‐9α,15α‐diol ( 3 ); and 3β‐acetoxy‐5α‐cholesta‐8(14),9(11)‐dien‐15α‐ol ( 4 ) have been aromatized to a 9∶1 mixture of 3β‐hydroxy‐12‐methyl‐18‐nor‐5α,17β(H)‐cholesta‐8,11,13‐triene ( 5a ) and 3β‐hydroxy‐12‐methyl‐18‐nor‐5α,17α(H)‐cholesta‐8,11,13‐triene ( 5b ) in ethanol solution by using hydrochloric acid. The aromatization by action of p ‐toluenesulfonic acid gave mainly the epimer with the natural C‐17 configuration as the acetate 5c at the appropriate p ‐toluenesulfonic acid concentration. 3β‐Acetoxy‐5α‐cholesta‐7,9(11),14‐triene ( 7a ) and 3β‐hydroxy‐5α‐cholesta‐8,11,14‐triene ( 8a ), 2 intermediary compounds in the aromatization, were isolated and characterized.