Short synthesis of 14,15-didehydro-E-deplancheine, presumed biosynthetic intermediate in the formation from geissoschizine, of Corynanthé alkaloids missing the three-carbon unit at C-15

Heterocycles

Volumn 43, Issue 2, 1996, Pages 443-446

  Lounasmaa, Mauri ^a   Hanhinen, Pirjo ^a   Jokela, Reija ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0347148575     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-95-7314     Document Type: Article

References (11)

1. J. LeMen and W.I. Taylor, Experientia, 1965, 21, 508.
2. M. Lounasmaa and A. Tolvanen, "The Monoterpenoid Indole Alkaloids", ed. by J.E. Saxton, 2nd Edition, Wiley, New York, 1994, pp. 57-159.
3. A.I. Scott, Bioorg. Chem., 1974, 3, 398. See also, C. Kan-Fan and H.-P. Husson, Tetrahedron Lett., 1980, 21, 4265.
4. A.I. Scott, Bioorg. Chem., 1974, 3, 398. See also, C. Kan-Fan and H.-P. Husson, Tetrahedron Lett., 1980, 21, 4265.
5. 3 is still applicable for the formation of deplancheine from geissoschizine.
6. 5: C, 65.61; H, 6.29; N, 7.29. Found C, 65.42; H, 6.10; N, 7.14.
7. M. Lounasmaa, P. Hanhinen, and R. Jokela, Tetrahedron, 1995, 51, 8623.
8. 2: 251.1532.
9. E.g. T. Tamminen, R. Jokela, B. Tirkkonen, and M. Lounasmaa, Tetrahedron, 1989, 45, 2683.
10. R. Jokela, A. Juntunen, and M. Lounasmaa, Planta Med., 1987, 53, 386.
11. A.I. Meyers, T. Sohda, and M.F. Loewe, J. Org. Chem., 1986, 51, 3108.