Efficient and scalable enantioselective synthesis of a CGRP antagonist

  • Org Lett. 2012 Sep 21;14(18):4938-41. doi: 10.1021/ol302262q.
David K Leahy  1 ,  Yu Fan ,  Lopa V Desai ,  Collin Chan ,  Jason Zhu ,  Guanglin Luo ,  Ling Chen ,  Ronald L Hanson ,  Masano Sugiyama ,  Thorsten Rosner ,  Nicolas Cuniere ,  Zhiwei Guo ,  Yi Hsiao ,  Qi Gao
Affiliations
  • 1. Chemical Development and Drug Product Science and Technology, Bristol-Myers Squibb Company, One Squibb Drive, New Brunswick, New Jersey 08903, USA. [email protected]
PMID: 22954228 DOI: 10.1021/ol302262q
Abstract

An enantioselective synthesis of the CGRP antagonist BMS-846372, amenable to large scale preparation, is presented. This new synthesis showcases a chemo- and enantioselective reduction of a cyclohepta[b]pyridine-5,9-dione as well as a Pd-catalyzed alpha-arylation reaction to form the key carbon-carbon bond and set the absolute and relative stereochemistry.

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