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