Synthesis of ultra-short-acting neuromuscular blocker GW 0430: a remarkably stereo- and regioselective synthesis of mixed tetrahydroisoquinolinium chlorofumarates.

Journal Article (Journal Article)

[formula: see text] The stereo- and regioselective synthesis of ultra-short-acting nondepolarizing neuromuscular blocker GW 0430 (5a) is described. Key steps involved the enantioselective transfer hydrogenation of imine 8 employing Noyori's catalyst, the stereoselective crystallization and methanolysis of trans-bataines 11 and 12, and the stereo- and regioselective trans elimination of hydrogen chloride from 14. The latter transformation allowed complete control of the position of the chloro substituent and stereochemistry at the double bond of the linker in 15.

Full Text

Duke Authors

Cited Authors

  • Samano, V; Ray, JA; Thompson, JB; Mook, RA; Jung, DK; Koble, CS; Martin, MT; Bigham, EC; Regitz, CS; Feldman, PL; Boros, EE

Published Date

  • December 16, 1999

Published In

Volume / Issue

  • 1 / 12

Start / End Page

  • 1993 - 1996

PubMed ID

  • 10836056

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol9911573

Language

  • eng

Conference Location

  • United States