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Org Lett. 2003 Aug 21;5(17):3155-8.

Efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921.

Author information

1
Process Research and Development, The Bristol-Myers Squibb Pharmaceutical Research Institute, P.O. Box 4000, Princeton, New Jersey 08543, USA. janak.singh@bms.com

Abstract

[reaction: see text] An efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921 was accomplished. Two short enantioselective syntheses of the common key intermediate (S)-alpha-aminoazepinone 6b were developed. Olefin 3 was converted to 6b via asymmetric hydrogenation. Alternatively, enyne 12 was converted to racemic alpha-aminoazepinone 15b, which was transformed to 6b by a practical dynamic resolution.

PMID:
12917005
DOI:
10.1021/ol0352308
[Indexed for MEDLINE]

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