Synthetic applications of 2-(1,3-dithian-2-yl)indoles Vl.1 Synthesis of 20-epidasycarpidone

Tetrahedron

Volumn 52, Issue 10, 1996, Pages 3563-3574

  Forns, Pilar ^a   Diez, Anna ^a   Rubiralta, Mario ^a   Solans, Xavier ^a   Font Bardia, Mercè ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

20 EPIDASYCARPIDONE; ALKALOID; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030068189     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00033-6     Document Type: Article

References (19)

1. Micouin, L.; Diez, A.; Castells, J.; López, D.; Rubiralta, M.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett., 1995, 36, 1693-1696.
2. Diez, A.; Castells, J.; Forns, P.; Rubiralta, M.; Grierson, D. S.; Husson H.-P.; Solans, X.; Font-Bardía, M. Tetrahedron, 1994, 50, 6585-6602.
3. The biogenetic numbering is used in this paper when referring to dasycarpidone-type compounds and alkaloids.
4. For biogenetic numbering, see: LeMen, J; Taylor, W.I. Experientia, 1965, 21, 508-509.
5. For the synthesis of dasycarpidone and its 20-epimer, see: (a) Jackson, A.; Wilson, N. D.V.; Gaskell, A. J.; Joule, J. A. J. Chem. Soc. C , 1969, 2738-2747;
6. (b) Dolby, L. J.; Biere, H. J. Org. Chem., 1970, 35, 3843-3845.
7. (c) Kametani, T.; Suzuki, T. J. J. Org. Chem., 1971, 36, 1291-1293;
8. (d) Gràcia, J.; Casamitjana, N.; Bonjoch, J.; Bosch, J. J. Org. Chem., 1994, 59, 3939-3951;
9. (e) Blechert, S.; Knier, R.; Schroers, H.; Wirth, T. Synthesis, 1995, 592-604.
10. 6b Ferrer, M.; Sánchez-Baeza, F.; Messeguer, A, unpublished results; (b) Ferrer, M.; Sánchez-Baeza, F.; Messeguer, A.; Diez, A.; Rubiralta, M. J. Chem. Soc., Chem. Commun., 1995, 293-294.
11. 6b Ferrer, M.; Sánchez-Baeza, F.; Messeguer, A, unpublished results; (b) Ferrer, M.; Sánchez-Baeza, F.; Messeguer, A.; Diez, A.; Rubiralta, M. J. Chem. Soc., Chem. Commun., 1995, 293-294.
12. Davis, D.A.; Gribble, G.W. Tetrahedron Lett., 1990, 31, 1081-1084.
13. Rubiralta, M.; Casamitjana, N.; Grierson, D.S.; Husson, H.-P. Tetrahedron, 1988, 44, 443-450.
14. In the basic reaction medium the indole nucleus bears a negative charge, and the cyclization occurs preferably from the nitrogen atom due to its electronegativity.
15. Rubiralta, M.; Torrens, A.; Reig, I.; Grierson, D.S.; Husson, H.-P. Heterocycles, 1989, 29, 2121-2133.
16. Stork, G.; Zhao, K. Tetrahedron Lett., 1989, 30, 287-290.
17. For the transformation of 20-epidasycarpidone into 20-epiuleine, see reference 5b.
18. 13C NMR of uleine and 20-epiuleine, see: Borris, R.P.; Lankin, D.C., Cordell, G.A. J. Nat. Prod., 1983, 46, 200-205.
19. -3, respectively. Tables of atomic coordinates, bond lengths and angles, and thermal parameters (supplementary material) are available on request from the Cambridge Crystallographic Data Center.