Regeneration of a Steroid C 13 Angular Methyl Group from a Functionalized Precursor : Application to the Preparation of C 18-2H3 Steroids and C 18-2H3 D-Homosteroids

Autor: Blair, IA, Frith, RG, Phillipou, G, Seaborn, CJ
Zdroj: Australian Journal of Chemistry; 1979, Vol. 32 Issue: 10 p2327-2330, 4p
Abstrakt: 3β-Acetoxypregn-5-eno-18,20-lactone has been converted into 3β,20β-dimethoxypregn-5-ene (6) by using electrochemical deoxygenation of a C13 formyl intermediate as a key reaction. The electrochemicalreduction is also shown to be applicable to multiple deuterium labelling of the C13 angular methyl group in high isotopic purity.A facile preparation of 3β -hydroxy-l7α-methyl-D-homoandrost-5-en-l7a-one (10) and its respective C18-2H3 analogue from the ether (6) is described.
Databáze: Supplemental Index