Issue 0, 1971

Steroidal analogues of unnatural configuration. Part III. Reactions of the Δ5-bond in 4,4,14α-trimethyl-19-nor-10α-pregn-5-ene derivatives

Abstract

The Δ5-bond of 4,4,14α-trimethyl-19-nor-10α-pregn-5-ene and related substances undergoes stereoselective attack with a variety of reagents. trans-Addition leads exclusively to 5α,6β-disubstituted products, while cis-addition favours α-face attack. Cleavage of the derived α- and β-epoxides also leads exclusively to 5α,6β-disubstituted products. It is demonstrated that a 6β-hydroxy-compound in the 19-nor-5α,10α-series undergoes intramolecular alkoxy-radical attack upon the 3-position.

Article information

Article type
Paper

J. Chem. Soc. C, 1971, 3929-3934

Steroidal analogues of unnatural configuration. Part III. Reactions of the Δ5-bond in 4,4,14α-trimethyl-19-nor-10α-pregn-5-ene derivatives

J. R. Bull, P. R. Enslin and H. H. Lachmann, J. Chem. Soc. C, 1971, 3929 DOI: 10.1039/J39710003929

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