Synthesis of 3-carboxy-20-keto steroid, SB 209963, a 5α-reductase inhibitor, by palladium-catalyzed hydroxycarbonylation

DOI: 10.1016/S0040-4039(99)00456-6

Source and publish data:

Tetrahedron Letters p. 3123 - 3124 (1999)

Update date:2022-08-03

Topics:

Authors:

Yu, Marvin S.

Baine, Neil H.

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Article abstract of DOI:10.1016/S0040-4039(99)00456-6

SB 209963 was produced in three steps starting from 17β- carboxyandrost-4-en-3-one. A palladium-catalyzed hydroxycarbonylation introduced the carboxylic acid under mild conditions withOUt epimerization at C17. This reaction represents the first example of hydroxycarbonylation of a vinyl halide under neutral conditions.

Full text of DOI:10.1016/S0040-4039(99)00456-6

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Product name:(8S,9S,10R,13S,14S,17S)-3-Bromo-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-17-carbonyl bromide

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