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

A new route to steroid ring C aromatization from readily available precursors / M. Anastasia, P. Allevi, A. Fiecchi, A. Scala. - In: LIPIDS. - ISSN 0024-4201. - 17:3(1982), pp. 226-229.

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

M. Anastasia
Primo
;
P. Allevi
Secondo
;
1982

Abstract

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
aromatic steroids ; acidic aromatization
Settore BIO/10 - Biochimica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/184449
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