Studies on the Oxidation of Aromatic Steroids
It was found that chromic acid oxidation of ring-A aromatic steroids containing a strong electron-donating C3-substituent, such as methoxyl, gave the corresponding 9-hydroxy-11-oxo derivative (ketol). However, a ketol was not formed if a C3-methoxyl substituted ring-A aromatic steroid also contained a substituent at C1.
When a C3-methoxyl substituent was present, the 6-oxo-ring-A aromatic steroid was a minor oxidation product but such compounds were the major products from the chromic acid oxidation of ring-A aromatic steroids containing a weak C3-electron-donating group, such as acetoxyl. The oxidation of a ring-A aromatic steroid containing a C2-methoxyl substituent gave an almost quantitative yield of the corresponding 6-oxo compound.
Suzuki103 has claimed that the major oxidation product of 17?-acetoxy-3-methoxyestra-1,3,5(10)-triene (34b) is 17 ?-acetoxy-9?- hydroxy-3-methoxyestra-1,3,5(10)-trien-11-one (123). Physical and chemical evidence are presented to show that this product is in fact the 9?-hydroxy epimer and a reaction pathway for its formation is proposed.
An examination of the oxidation products of a ring-B aromatic steroid and a ring-C aromatic steroid shows that no ketols were formed.
School Location:New Zealand
Source Type:Master's Thesis
Keywords:fields of research 250000 chemical sciences
Date of Publication:01/01/1968