Efficient Asymmetric Synthesis of the Vasopeptidase Inhibitor BMS-189921

Autor: Singh, J., Kronenthal, D. R., Schwinden, M., Godfrey, J. D., Fox, R., Vawter, E. J., Zhang, B., Kissick, T. P., Patel, B., Mneimne, O., Humora, M., Papaioannou, C. G., Szymanski, W., Wong, M. K. Y., Chen, C. K., Heikes, J. E., DiMarco, J. D., Qiu, J., Deshpande, R. P., Gougoutas, J. Z., Mueller, R. H.
Zdroj: Organic Letters; August 2003, Vol. 5 Issue: 17 p3155-3158, 4p
Abstrakt: 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.
Databáze: Supplemental Index