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

✍ Scribed by Marvin S. Yu; Neil H. Baine

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
121 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

SB 209963 was produced in three steps starting from 17[3-carboxyandrost-4-en-3-one. A palladiumcatalyzed hydroxycarbonylation introduced the carboxylic acid under mild conditions without epimerization at C-17. This reaction represents the first example of hydroxycarbonylation of a vinyl halide under neutral conditions.

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