Enantioselective synthesis of poison-frog alkaloid 237D and determination of absolute stereochemistry

Heterocycles

Volumn 65, Issue 1, 2005, Pages 5-8

  Toyooka, Naoki ^a   Kawasaki, Masashi ^b   Nemoto, Hideo ^a   Daly, John W ^c   Spande, Thomas F ^c   Garraffo, H Martin ^c  

^a UNIVERSITY OF TOYAMA   (Japan)

^b TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^c NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 19644379588     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-04-10269     Document Type: Article

References (11)

1. Daly J.W., Garraffo H.M., and Spande T.F. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives Vol. 13 (1999), Pergamon Press, Cambridge 1-161
2. Daly J.W. In: Cordell G.A. (Ed). The Alkaloids Vol. 50 (1998), Academic Press, New York 141-169
3. Daly J.W., Kaneko T., Wilham J., Garraffo H.M., Spande T.F., Espinosa A., and Donnelly M. Proc. Nat'l Acad. USA 99 (2002) 13996
4. Tokuyama T., Nishimori N., Shimada A., Edwards M.W., and Daly J.W. Tetrahedron 43 (1987) 643. The detection of 237D in the Dendrobates. pumilio extract is a new finding. Alkaloid 235B′ from D. pumilio and (-)-7 could not be separated with a non-chiral column, indicating the likelihood that the small amount of (-)-237D in the two extracts recently examined was missed earlier, but is detectible with the chiral column and the very slow temperature program used in the present work.
5. Edwards M.W., Daly J.W., and Myers C.W. J. Nat. Prod. 51 (1988) 1188. The detection of 237D in the Dendrobates. pumilio extract is a new finding. Alkaloid 235B′ from D. pumilio and (-)-7 could not be separated with a non-chiral column, indicating the likelihood that the small amount of (-)-237D in the two extracts recently examined was missed earlier, but is detectible with the chiral column and the very slow temperature program used in the present work.
6. Toyooka N., Fukutome A., Shinoda H., and Nemoto H. Angew. Chem., Int. Ed. 42 (2003) 3808
7. Toyooka N., Fukutome A., Shinoda H., and Nemoto H. Tetrahedron 60 (2004) 6197
8. Momose T., and Toyooka N. J. Org. Chem. 59 (1994) 943
9. Toyooka N., Tanaka K., Momose T., Daly J.W., and Garraffo H.M. Tetrahedron 53 (1997) 9553
10. 3).
11. Corey E.J., and Yuen P. Tetrahedron Lett. 30 (1989) 5825