Total Synthesis of the Proposed Structures of Indole Alkaloids Lyaline and Lyadine

Journal of Organic Chemistry

Volumn 69, Issue 3, 2004, Pages 752-756

  Bennasar, M Lluïsa ^a   Roca, Tomàs ^a   Monerris, Manuel ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEAR MAGNETIC RESONANCE; SYNTHESIS (CHEMICAL);

NATURAL PRODUCTS;

ORGANIC COMPOUNDS;

INDOLE ALKALOID; LYADINE; LYALINE; PAURIDIANTHA LYALLI EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; COMPARATIVE STUDY; DEACYLATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PAURIDIANTHA LYALLI; REACTION ANALYSIS; RUBIACEAE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

INDOLE ALKALOIDS; LITHIUM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PYRIDINES; RUBIACEAE;

EID: 0842264143     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035507h     Document Type: Article

References (35)

1. Pousset, J. L.; Levesque, J.; Cavé, A.; Picot, F.; Potier, P.; Paris, R. R. Plantes Med. Phytother. 1974, 8, 51-56.
2. Levesque, J.; Pousset, J. L.; Cavé, A.; Cavé, A. C. R. Acad. Sci. Paris C 1974, 278, 959-961.
3. Levesque, J.; Pousset, J. L.; Cavé, A. C. R. Acad. Sci. Paris C 1974, 279, 1053-1055.
4. Kisakürek, M. V.; Leeuwenberg, A. J. M.; Hesse, M. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1983; Chapter 5.
5. (a) Levesque, J.; Pousset, J.-L.; Cavé, A. C. R. Acad. Sci. Paris C 1975, 280, 593-595.
6. (b) Levesque, J.; Jacquesy, R.; Foucher, J. P. Tetrahedron 1982, 38, 1417-1424.
7. This two-step biogenetic transformation is believed to operate in other indolopyridine alkaloids. For a recent example, see: Takayama, H.; Tsutsumi, S. ; Kitajima, M.; Santiarworn, D.; Liawruangrth B.; Aimi, N. Chem. Pharm. Bull. 2003, 51, 232-233.
8. Levesque, J.; Jacquesy, R.; Merienne, C. J. Nat. Prod. 1983, 46, 619-625.
9. Aimi, N.; Murakami, H.; Tsuyuki, T.; Nishiyama, T.; Sakai, S.; Haginiwa, J. Chem. Pharm. Bull. 1986, 34, 3064.
10. Aimi, N.; Seki, H.; Sakai, S. Chem. Pharm. Bull. 1992, 40, 2588-2590.
11. For reviews on the chemistry of dihydropyridines, see: (a) Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1-42.
12. (b) Stout, D.; Meyers, A. I. Chem. Rev. 1982, 82, 223-243.
13. (c) Sausins, A.; Duburs, G. Heterocycles 1988, 27, 291-814.
14. (d) Lavilla, R. J. Chem. Soc., Perkin Trans. 1 2002, 1141-1156.
15. See inter alia: (a) Comins, D. L.; Abdullah, A. H. J. Org. Chem. 1982, 47, 4315-4319.
16. (b) Comins, D. L.; Stroud, E. D.; Herrick, J. J. Heterocycles 1984, 22, 151-157.
17. (d) Akiba, K.; Iseki, Y.; Wada, M. Bull. Chem. Soc. Jpn. 1984, 57, 1994-1999.
18. (e) Mangeney, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877-1888.
19. (f) Yamada, S.; Misono, T.; Ichikawa, M.; Morita, C. Tetrahedron 2001, 57, 8939-8949.
20. (a) Bennasar, M.-L.; Vidal, B.; Bosch, J. J. Org. Chem. 1997, 62, 3597-3609.
21. (b) Bennasar, M.-L.; Juan, C.; Bosch, J. Tetrahedron Lett. 1998, 39, 9275-9278.
22. (c) Bennasar, M.-L.; Vidal, B.; Kumar, R.; Lázaro, A.; Bosch, J. Eur. J. Org. Chem. 2000, 3919-3925.
23. (d) Bennasar, M.-L.; Zulaica, E.; Juan, C.; Alonso, Y.; Bosch, J. J. Org. Chem. 2002, 67, 7465-7474.
24. (e) Bennasar, M.-L.; Roca, T.; Monerris, M.; Juan, C.; Bosch, J. Tetrahedron 2002, 58, 8099-8106.
25. For the use of an intramolecular enamide addition to a 3,5-disubstituted N-acylpyridinium salt in the synthesis of indolopyridine alkaloids, see: (a) Lavilla, R.; Gullón, F.; Bosch, J. Eur. J. Org. Chem. 1999, 373, 3-378.
26. (a) Karrer, P.; Müller, H. J. Org. Chem. 1957, 22, 1433-1434.
27. (b) Seki, H.; Hashimoto, A.; Hino, T. Chem. Pharm. Bull. 1993, 41, 1169-1172.
28. Bracher, F.; Papke, T. Monatsh. Chem. 1995, 126, 805-809.
29. Bennasar, M.-L.; Zulaica, E.; Roca, T.; Alonso, Y.; Monerris, M. Tetrahedron Lett. 2003, 44, 4711-4744.
30. The corresponding copper-catalyzed Grignard reagent and the lower order cyanocuprate gave mixtures of dihydropyridines in poor yields.
31. For the use of this type of organometallic in the synthesis of 4-benzylpyridines, see: (a) Chia, W.-L.; Shiao, M.-J. Tetrahedron Lett. 1991, 32, 2033-2034.
32. (b) Shing, T.-L.; Chia, W.-L.; Shiao, M.-J.; Chau, T.-Y. Synthesis 1991, 849-850.
33. Pabel, J.; Hösl, C. E.; Maurus, M.; Ege, M.; Wanner, K. Th. J. Org. Chem. 2000, 65, 9272-9275.
34. Lavilla, R.; Gotsens, T.; Guerrero, M.; Bosch, J. Synthesis 1995, 382-384.
35. 19-H is reported to appear at δ 5.7 in ref 1.