Spirocyclization strategy toward indole phytoalexins. The first synthesis of (±)-1-methoxyspirobrassinin, (±)-1-methoxyspirobrassinol, and (±)-1-methoxyspirobrassinol methyl ether

Tetrahedron Letters

Volumn 43, Issue 52, 2002, Pages 9489-9492

  Kutschy, Peter ^a   Suchý, Mojmír ^a   Monde, Kenji ^b   Harada, Nobuyuki ^c   Marušková, Renata ^a   Čurillová, Zuzana ^a   Dzurilla, Milan ^a   Miklošová, Mariana ^a   Mezencev, Roman ^a   Mojžiš, Ján ^a  

^a P J AFÁRIK UNIVERSITY   (Slovakia)

^b HOKKAIDO UNIVERSITY   (Japan)

^c Institute of Multidisciplinary Research for Advanced Materials   (Japan)

Author keywords

Antitumor activity; Dioxane dibromide; Indoles; Phytoalexins; Spirocyclization

Indexed keywords

1 METHOXYSPIROBRASSININ; 1 METHOXYSPIROBRASSINOL; 1 METHOXYSPIROBRASSINOL METHYL ETHER; CYCLOBRASSININ; DIOXANE DERIVATIVE; PHYTOALEXIN; SPIROBRASSININ; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CHEMICAL REACTION; CHROMATOGRAPHY; CONTROLLED STUDY; DIASTEREOISOMER; DRUG SYNTHESIS; HUMAN; HUMAN CELL; OXIDATION; SPECTROSCOPY; SPIROCYCLIZATION; STEREOCHEMISTRY;

EID: 18744396053     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02452-8     Document Type: Article

References (21)

1. Purkayastha R.P. Progress in phytoalexin research during the past 50 years. Daniel M., Purkayastha R.P. Handbook of Phytoalexin Metabolism and Action. 1995;1-39 Marcel Dekker, New York.
2. For a recent review on cruciferous indole phytoalexins see: Pedras M.S.C., Okanga F.I., Zaharia I.L., Khan A.Q. Phytochemistry. 53:2000;161-176.
3. Mehta R.G., Liu J., Constantinou A., Hawthorne M., Pezzuto J.M., Moon R.C., Moriarty R.M. Anticancer Res. 14:1994;1209-1214.
4. Mehta R.G., Liu J., Constantinou A., Thomas C.F., Hawthorne M., You M., Gerhäuser C., Pezzuto J.M., Moon R.C., Moriarty R.M. Carcinogenesis. 16:1995;399-404.
5. Sabol M., Kutschy P., Siegfried L., Miroššay A., Suchý M., Hrbková H., Dzurilla M., Marušková R., Starková J., Paulíková E. Biologia (Bratislava). 55:2000;701-707.
6. Moody C.J., Roffey J.R.A., Stephens M.A., Stradford I.J. Anti-Cancer Drugs. 8:1997;489-499.
7. Takasugi M., Monde K., Katsui N., Shirata A. Chem. Lett. 1987;1631-1632.
8. Monde K., Sasaki K., Shirata A., Takasugi M. Phytochemistry. 30:1991;2915-2917.
9. Suchý M., Kutschy P., Monde K., Goto H., Harada N., Takasugi M., Dzurilla M., Balentová E. J. Org. Chem. 66:2001;3940-3947.
10. Gross D., Porzel A., Schmidt J. Z. Naturforsch., Sect. C. 49:1994;281-285.
11. Monde K., Takasugi M., Shirata A. Phytochemistry. 39:1995;581-586.
12. For a review on 1-hydroxyindoles see: Somei M. Heterocycles. 50:1999;1157-1211.
13. Monde K., Takasugi M., Ohnishi T. J. Am. Chem. Soc. 116:1994;6650-6657.
14. Takasugi M., Monde K., Katsui N., Shirata A. Bull. Chem. Soc. Jpn. 61:1988;285-289.
15. Pedras M.S.C., Zaharia I.L. Phytochemistry. 55:2000;213-216.
16. Kutschy P., Dzurilla M., Takasugi M., Török M., Achbergerová I., Homzová R., Rácová M. Tetrahedron. 54:1998;3549-3566.
17. 3); EIMS identical with 14a.
18. Kawasaki T., Somei M. Heterocycles. 31:1990;1605-1608.
19. Somei M., Kobayashi K., Shimizu K., Kawasaki T. Heterocycles. 33:1992;77-80.
20. Mosmann T. J. Immunol. Methods. 65:1983;155-163.
21. Wattenberg L.W. Cancer Res. 52:1992;2085-2091.