Literature DB >> 12917005

Efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921.

Janak Singh1, David R Kronenthal, Mark Schwinden, Jollie D Godfrey, Rita Fox, Edward J Vawter, Bo Zhang, Thomas P Kissick, Bharat Patel, Omar Mneimne, Michael Humora, Chris G Papaioannou, Walter Szymanski, Michael K Y Wong, Chien K Chen, James E Heikes, John D DiMarco, Jun Qiu, Rajendra P Deshpande, Jack Z Gougoutas, Richard H Mueller.   

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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Year:  2003        PMID: 12917005     DOI: 10.1021/ol0352308

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

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Authors:  Jonathan W Bogart; Albert A Bowers
Journal:  Org Biomol Chem       Date:  2019-04-10       Impact factor: 3.876

2.  Facile conversion of chromane-6-triflate to chromane-6-alanines under Palladium conditions.

Authors:  Daniel K Miller
Journal:  Tetrahedron Lett       Date:  2013-02-20       Impact factor: 2.415

3.  Crystal structure of N-(tert-but-oxy-carbon-yl)glycyl-(Z)-β-bromo-dehydro-alanine methyl ester [Boc-Gly-(β-Br)((Z))ΔAla-OMe].

Authors:  Paweł Lenartowicz; Maciej Makowski; Bartosz Zarychta; Krzysztof Ejsmont
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-11-29
  3 in total

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