Efficient Asymmetric Synthesis of the Vasopeptidase Inhibitor BMS-189921

An efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921 was accomplished. Two short enantioselective syntheses of the common key intermediate (S)-α-aminoazepinone 6b were developed. Olefin 3 was converted to 6b via asymmetric hydrogenation. Alternatively, enyne 12 was converted t...

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Veröffentlicht in:	Organic letters 2003-08, Vol.5 (17), p.3155-3158
Hauptverfasser:	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
Format:	Artikel
Sprache:	eng
Schlagworte:	Azepines - chemical synthesis Azepines - chemistry Azepines - pharmacology Endothelium, Vascular - enzymology Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - pharmacology Hydrogenation Neprilysin - antagonists & inhibitors Stereoisomerism
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Beschreibung
Zusammenfassung:	An efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921 was accomplished. Two short enantioselective syntheses of the common key intermediate (S)-α-aminoazepinone 6b were developed. Olefin 3 was converted to 6b via asymmetric hydrogenation. Alternatively, enyne 12 was converted to racemic α-aminoazepinone 15b, which was transformed to 6b by a practical dynamic resolution.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol0352308