Organic Letters, volume 5, issue 17, pages 3155-3158
Efficient Asymmetric Synthesis of the Vasopeptidase Inhibitor BMS-189921
Janak Singh
1
,
David R Kronenthal
1
,
Mark Schwinden
1
,
Jollie D. Godfrey
1
,
Rita Fox
1
,
Edward J Vawter
1
,
Bo Zhang
1
,
Thomas P Kissick
1
,
Bharat Patel
1
,
Omar Mneimne
1
,
Michael Humora
1
,
Chris G Papaioannou
1
,
Walter Szymanski
1
,
Michael K.Y. Wong
1
,
Chien K Chen
1
,
James E Heikes
1
,
John D Dimarco
1
,
Jun Qiu
1
,
Rajendra P. Deshpande
1
,
Jack Z. Gougoutas
1
,
Richard H Mueller
1
1
Process Research and Development, The Bristol-Myers Squibb Pharmaceutical Research Institute, P.O. Box 4000, Princeton, New Jersey 08543, Process Research and Development, The Bristol-Myers Squibb Pharmaceutical Research Institute, 1 Squibb Drive, New Brunswick, New Jersey 08903, and Solid State Chemistry, The Bristol-Myers Squibb Pharmaceutical Research Institute, Princeton, New Jersey 08543
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Publication type: Journal Article
Publication date: 2003-08-01
Journal:
Organic Letters
scimago Q1
SJR: 1.245
CiteScore: 9.3
Impact factor: 4.9
ISSN: 15237060, 15237052
PubMed ID:
12917005
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
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.
Found
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