Alkylated Steroids. Part 4. An Unusual Favorskii Rearrangement

DOI: 10.1039/P19810002631

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2631 - 2636 (1981)

Update date:2022-08-03

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Authors:

Logan, Robert T.

Roy, Robert G.

Woods, Gilbert F.

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Article abstract of DOI:10.1039/P19810002631

Favorskii rearrangement of the mixed 17ξ-bromo-16α-methyl-20-oxo-5α-pregn-9(11)-en-3β-yl acetates (5) and (6) (9:1) gives methyl 3β-hydroxy-16α,17α-dimethyl-5α-androst-9(11)-ene-17-carboxylate (7) and methyl 3β-hydroxy-16α-methyl-5α-pregn-9(11)-en-21-oate (9) as the major components.Only a small amount of the isomeric 16α,17β-dimethyl-17-carboxylate (8) is formed.The structures of the esters (7) and (9) are confirmed by synthesis, and an explanation for the unexpected formation of (9) is advanced.

Full text of DOI:10.1039/P19810002631

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