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Efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921 |
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| Authors: | Singh Janak Kronenthal David R Schwinden Mark Godfrey Jollie D Fox Rita Vawter Edward J Zhang Bo Kissick Thomas P Patel Bharat Mneimne Omar Humora Michael Papaioannou Chris G Szymanski Walter Wong Michael K Y Chen Chien K Heikes James E DiMarco John D Qiu Jun Deshpande Rajendra P Gougoutas Jack Z Mueller Richard H |
| Institution: | 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. |
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