Synthesis of ultra-short-acting neuromuscular blocker GW 0430: a remarkably stereo- and regioselective synthesis of mixed tetrahydroisoquinolinium chlorofumarates.
Publication
, Journal Article
Samano, V; Ray, JA; Thompson, JB; Mook, RA; Jung, DK; Koble, CS; Martin, MT; Bigham, EC; Regitz, CS; Feldman, PL; Boros, EE
Published in: Org Lett
December 16, 1999
[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.
Duke Scholars
Altmetric Attention Stats
Dimensions Citation Stats
Published In
Org Lett
DOI
ISSN
1523-7060
Publication Date
December 16, 1999
Volume
1
Issue
12
Start / End Page
1993 / 1996
Location
United States
Related Subject Headings
- Stereoisomerism
- Organic Chemistry
- Neuromuscular Blocking Agents
- Methanol
- Isoquinolines
- Crystallization
- 34 Chemical sciences
- 03 Chemical Sciences
Citation
APA
Chicago
ICMJE
MLA
NLM
Samano, V., Ray, J. A., Thompson, J. B., Mook, R. A., Jung, D. K., Koble, C. S., … Boros, E. E. (1999). Synthesis of ultra-short-acting neuromuscular blocker GW 0430: a remarkably stereo- and regioselective synthesis of mixed tetrahydroisoquinolinium chlorofumarates. Org Lett, 1(12), 1993–1996. https://doi.org/10.1021/ol9911573
Samano, V., J. A. Ray, J. B. Thompson, R. A. Mook, D. K. Jung, C. S. Koble, M. T. Martin, et al. “Synthesis of ultra-short-acting neuromuscular blocker GW 0430: a remarkably stereo- and regioselective synthesis of mixed tetrahydroisoquinolinium chlorofumarates.” Org Lett 1, no. 12 (December 16, 1999): 1993–96. https://doi.org/10.1021/ol9911573.
Samano V, Ray JA, Thompson JB, Mook RA, Jung DK, Koble CS, et al. Synthesis of ultra-short-acting neuromuscular blocker GW 0430: a remarkably stereo- and regioselective synthesis of mixed tetrahydroisoquinolinium chlorofumarates. Org Lett. 1999 Dec 16;1(12):1993–6.
Samano, V., et al. “Synthesis of ultra-short-acting neuromuscular blocker GW 0430: a remarkably stereo- and regioselective synthesis of mixed tetrahydroisoquinolinium chlorofumarates.” Org Lett, vol. 1, no. 12, Dec. 1999, pp. 1993–96. Pubmed, doi:10.1021/ol9911573.
Samano V, Ray JA, Thompson JB, Mook RA, Jung DK, Koble CS, Martin MT, Bigham EC, Regitz CS, Feldman PL, Boros EE. Synthesis of ultra-short-acting neuromuscular blocker GW 0430: a remarkably stereo- and regioselective synthesis of mixed tetrahydroisoquinolinium chlorofumarates. Org Lett. 1999 Dec 16;1(12):1993–1996.
Published In
Org Lett
DOI
ISSN
1523-7060
Publication Date
December 16, 1999
Volume
1
Issue
12
Start / End Page
1993 / 1996
Location
United States
Related Subject Headings
- Stereoisomerism
- Organic Chemistry
- Neuromuscular Blocking Agents
- Methanol
- Isoquinolines
- Crystallization
- 34 Chemical sciences
- 03 Chemical Sciences