Steroid hormones. XXI. Some testosterone derivatives substituted at C19

Abstract

Addition of but-1-en-3-one to (1) produced the adducts (28) and (2b) which undergo ring fission with acid to give (3). Methylmagnesium iodide on (2a) and (2b) gives the alcohol mixture (4) which is converted by acid into (5). A similar series of reactions with derivatives of l,2-dihydrooestrone methyl ether gives the steroid (10) and the 17β-OH analogue, and (11) containing an angular isoprene unit.