566-29-0Relevant articles and documents
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Fieser,Nakanishi,Huang
, p. 4719 (1953)
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A New Route to Steroid Ring-c Aromatization from 7-Oxygenated Steroids
Anastasia, Mario,Ciuffreda, Pierangela,Puppo, Marina Del,Fiecchi, Alberto
, p. 587 - 590 (2007/10/02)
3β-Acetoxy-5α-cholesta-8,14-dien-7β-ol (3), 3β-acetoxy-8α,9α-epoxy-5α-cholestan-7β-ol (6a), and 3β-acetoxy-8α,14α-epoxy-5α-cholestan-7β-ol (8a) have been aromatized with hydrochloric acid in ethanol to afford a 9:1 mixture of 12-methyl-18-nor-5α,17β(H)-cholesta-8,11,13-trien-3β-ol (4) and 12-methyl-18-nor-5α-cholesta-8,11,13-trien-3β-ol (5).By the same acidic treatment 3β-acetoxy-8α,9α-epoxy-5α-cholestan-7α-ol (6c) generates 3β-hydroxy-5α-cholest-8-en-7-one (7a), and 3β-acetoxy-8α,14α-epoxy-5α-cholestan-7α-ol (8c) affords 3β-hydroxy-5α-cholest-8(14)-en-7-one (9a) accompanied by the previously unobserved 3β-hydroxy-5α-cholest-8(14)-en-15-one (10a).