Microbiological conversion of sterol derivatives to 5-androsten-17-one derivatives and their use

US4170518A · kind A · utility

Assignee

• SCHERING CORPORATION · US

Inventors

• Alfred Weber · Wien, AT
• Mario Kennecke · Berlin, DE
• Alfred Popper · Berlin, DE
• Rudolf Muller · Frankfurt, DE
• Ulrich Eder · Berlin, DE
• Gregor Haffer · Berlin, DE
• Gerhard Sauer · Berlin, DE
• Gunter Neef · Berlin, DE
• Rudolf Wiechert · Berlin, DE

Key dates

• Filing date: Jul 30, 1976
• Grant date: Oct 9, 1979
• Expiry date: Jul 30, 1996

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C12P33/005
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Sterol derivatives of the formula ##STR1## wherein R.sub.1 is a hydrogen atom and R.sub.2 is lower alkoxy, or R.sub.1 and R.sub.2 collectively are lower alkylenedioxy and R.sub.3 is a sterol hydrocarbon side chain are converted to the corresponding androsten-17-ones by the oxidative degradation activity of a species of microorganism which degrades sterol side chains, preferably of the genus Mycobacterium. The ether group of those compounds wherein R.sub.1 is a hydrogen atom and R.sub.2 is lower alkoxy, and the corresponding 17.beta.-hydroxy and 17.alpha.-hydrocarbon-17.beta.-hydroxy compounds is cleaved by reaction with an alkanoic acid chloride or anhydride in the presence of a Lewis acid.