Synthesis of Indole Phytoalexins Brassinin and Cyclobrassinin via [1-(tert-Butoxycarbonyl)indol-3-yl]-methyl Isothiocyanate as the Key Biomimetic Intermediate

Synlett

Volumn 1997, Issue 3, 1997, Pages 289-290

  Kutschy, Peter ^a   Achbergerová, Ingrid ^a   Dzurilla, Milan ^a   Takasugi, Mitsuo ^b  

^a P J AFÁRIK UNIVERSITY   (Slovakia)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003013914     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-761     Document Type: Article

References (30)

1. Purkayastha, R. P. in Handbook of Phytoalexins Metabolism and Action; Daniel, M.; Purkayastha, R. P., Eds.; Marcel Dekker: New York, 1995; p 1.
2. Gross, D. J. Plant. Dis. Prot. 1993, 100, 433.
3. Rouxel, T.; Kollman, A.; Belesdent, M-H. in Handbook of Phytoalexins Metabolism and Action; Daniel, M.; Purkayastha, R. P., Eds.; Marcel Dekker: New York, 1995; p 229.
4. Takasugi, M.; Katsui, N.; Shirata, A. J. Chem. Soc., Chem. Commun. 1986, 1077.
5. Takasugi, M.; Monde, K.; Katsui, N.; Shirata, A. Bull. Chem. Soc. Jpn. 1988, 61, 285.
6. Schallenberg, J.; Meyer, E. Z. Naturforsch. 1983, 38b, 108.
7. Yamada, F.; Kobayashi, K.; Shimizu, A.; Aoki, N.; Somei M. Heterocycles 1993, 36, 2783.
8. Mehta, R. G.; Liu, J.; Constantinou, A.; Thomas, C. F.; Hawthorne, H.; You, M.; Gerhäuser, C.; Pezzuto, J. M.; Moon, R. C.; Moriarty, R. M. Carcinogenesis, 1995, 16, 399.
9. Somei, M.; Kobayashi, K.; Shimizu, K.; Kawasaki, T. Heterocycles, 1992, 33, 77.
10. Mehta, R. G.; Liu, J.; Constantinou, A.; Hawthorne, M.; Pezzuto, J. M.; Moon, R. C.; Moriarty, R. M. Anticancer Res. 1994, 14, 1209.
11. Monde, K.; Takasugi, M.; J. Chem. Soc., Chem. Commun. 1991, 1582.
12. Monde, K.; Takasugi, M.; Ohnishi, T. J. Am. Chem. Soc. 1994, 116, 6650.
13. The first step in the biosynthesis of indole glucosinolates in oil-seed rape and Chinese cabbage involve the formation of indole-3-carboxaldehyde oxime from L-tryptophan: Bennett, R.; Ludwig-Muller, J.; Kiddle, G.; Hilgenberg, W.; Wallsgrove, R. Planta, 1995, 196, 239.
14. Hanley, A. B.; Parsley, K. R. Phytochemistry, 1990, 29, 769.
15. Putochin, N. Ber. Deut. Chem. Ges. 1926,59, 1987.
16. Jochims, J.C.; Seeliger, A. Angew. Chem., 1967, 79, 151.
17. Staab, H. A.; Walter, G. Liebigs. Ann. Chem. 1962, 657, 104.
18. Spectral data and melting points of aldehydes 2a-2c are in agreement with those, reported in literature: Wackerle, L.; Ugi, I. Synthesis 1975, 598; Gribble, G. W.; Keavy, D.; Davis, D. A.; Saulnier, M. G.; Pelcman, B.; Barden, T. C.; Sibi, M. P.; Olson, E. R.; BelBruno, J. J. J. Org. Chem., 1992, 57, 5878; Vangvearvong, S.; Nichols, D. E. J. Org. Chem. 1995, 60, 3409.
19. Spectral data and melting points of aldehydes 2a-2c are in agreement with those, reported in literature: Wackerle, L.; Ugi, I. Synthesis 1975, 598; Gribble, G. W.; Keavy, D.; Davis, D. A.; Saulnier, M. G.; Pelcman, B.; Barden, T. C.; Sibi, M. P.; Olson, E. R.; BelBruno, J. J. J. Org. Chem., 1992, 57, 5878; Vangvearvong, S.; Nichols, D. E. J. Org. Chem. 1995, 60, 3409.
20. Spectral data and melting points of aldehydes 2a-2c are in agreement with those, reported in literature: Wackerle, L.; Ugi, I. Synthesis 1975, 598; Gribble, G. W.; Keavy, D.; Davis, D. A.; Saulnier, M. G.; Pelcman, B.; Barden, T. C.; Sibi, M. P.; Olson, E. R.; BelBruno, J. J. J. Org. Chem., 1992, 57, 5878; Vangvearvong, S.; Nichols, D. E. J. Org. Chem. 1995, 60, 3409.
21. Pedras, M. S. C.; Taylor, J. L. J. Nat. Prod. 1993, 56, 731.
22. Ipakschi, J. Chem. Ber. 1984, 117, 856.
23. Osby, J. O.; Ganem, B. Tetrahedron Lett. 1985, 26, 6413.
24. Lloyd, D. H.; Nichols, D. E. J. Org. Chem. 1986, 51, 4294.
25. Sharma, S. Synthesis 1978, 803.
26. + 288 (52), 232 (80), 215 (10), 174 (57), 130 (100), 102 (10), 57 (90).
27. Dhanak, D.; Reese, C. B. J. Chem. Soc., Perkin Trans. 1 1986, 2181.
28. Wensbo, D.; Annby, U.; Gronovitz, S. Tetrahedron 1995, 51, 10323.
29. Doyle, K. J.; Moody, C. J. Synthesis 1994, 1021.
30. 5 132-133°C.