A new route to steroid ring C aromatization from readily available precursors | Zendy

Anastasia Mario | Zendy; Allevi Pietro | Zendy; Fiecchi Alberto | Zendy; Scala Antonio | Zendy

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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.

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