Issue 13, 1975
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

A new and convenient synthesis of the 17α,21-diacetoxy-20-oxopregnane side-chain

Robin B. Boar,   James F. McGhie,   Mick Robinson  and  Derek H. R. Barton  

Abstract

A convenient ‘one-pot’ synthesis of the corticosteroid side chain has been developed. 20-Oxopregnane oximes have been converted into 20-acetylamino-17(20)-ene derivatives, which with lead tetra-acetate in dry benzene afford 17α-acetoxy-20-acetylimines. The latter are rearranged by acid to 20-enamides [as (IV)]. Further reaction with lead tetra-acetate then introduces an acetoxy-group at C-21. The 20-acetylimines are hydrolysed to the corresponding ketones by aqueous acid. Overall yields are high. Some preliminary experiments with 16α- and 16β-methylpregnanes are outlined.

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Article information

DOI
https://doi.org/10.1039/P19750001242
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1975, 1242-1244

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A new and convenient synthesis of the 17α,21-diacetoxy-20-oxopregnane side-chain

R. B. Boar, J. F. McGhie, M. Robinson and D. H. R. Barton, J. Chem. Soc., Perkin Trans. 1, 1975, 1242 DOI: 10.1039/P19750001242

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