Steroids and related studies. Part 49. 7a-Aza-B-homo[7a,7-d]tetrazole analogues of progesterone and testosterone

Abstract

We report the syntheses of tetrazole analogues of progesterone and testosterone, namely, 7a-aza-B-homopregn-4-erro[7a,7-d]tetrazole-3,20-dione (1) and 3-oxo-7a-aza-B-homoandrost-4-eno[7a,7-d]tetrazol-17β-y1 acetate (2), respectively. (25R)-7a-Aza-B-homospirost-5-eno[7a,7-d]tetrazol-3β-yl acetate (6) on Marker degradation gave 20-oxo-7a-aza-B-homopregna-5,16-dieno[7a,7-d]tetrazol-3β-y1 acetate (7). The compound (7) on selective hydrogenation followed by hydrolysis and Oppenauer oxidation yielded (1). 7a-Aza-B-homoandrost-5-eno[7a,7-d]tetrazole-3β,17β-diol diacetate (13) was partially hydrolysed to the alcohol (15), which on Oppenauer oxidation gave (2).