Steroids. Part XXXI. Attempted modification of the 14α-methyl group in 4,4,14α-trimethyl steroids

Abstract

5α-Lanost-8-en-3β-yl acetate was converted by way of 3β-acetoxy-5α-lanost-8-en-7-one into 3β-acetoxy-7α-hydroxy-5α-lanost-8-ene, which as the 7α-nitrite did not undergo the Barton reaction, and which with lead tetra-acetate–iodine gave 3β-acetoxy-5α-lanosta-7,9(11)-diene. 3β-Acetoxy-5α-lanost-9(11)-en-7-one, when hydrogenated over platinum in ethyl acetate–perchloric acid gave only 3β-acetoxy-5α-lanosta-7,9(11)-diene, whilst use of sodium borohydride yielded mainly 3β-acetoxy-7β-hydroxy-5α-lanost-9(11)-ene. Reductive cleavage of the 7β,8β-epoxide of 3β-acetoxy-5α-lanosta-7,9(11)-diene also yielded a 7β-hydroxy-5α-lanost-9(11)-ene; the 7α,8α-epoxide of 3β-acetoxy-5α-lanosta-7,9(11)-diene could not be prepared.