Synthesis of nectrisine and related compounds, and their biological evaluation

Tetrahedron

Volumn 55, Issue 28, 1999, Pages 8353-8364

  Kim, Yong Jip ^a   Takatsuki, Akira ^b   Kogoshi, Naoto ^a,b   Kitahara, Takeshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDASE INHIBITOR; NECTRISINE; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; CYCLIZATION; DERIVATIZATION; DRUG ISOLATION; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME INHIBITOR COMPLEX; HYDROXYLATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033538658     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00459-7     Document Type: Article

References (20)

1. 1) a) Merrer, Y L.; Poitout, L.; Depezay, J. D.; Dosbaa, I.; Geoffroy, S.; Foglietti, Foglietti, M. J. Bioorganic & Medicinal Chemistry 1997, 5, 519.
2. b) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199 and references cited therein.
3. 2) a) Furukawa, J.; Okuda, S.; Saito, K.; Hatanaka, S.I.; Phytochemistry 1985, 24, 593.
4. b) Nash, R.J.; Bell. E.A.; Williams, J.M. Phytochemistry 1985, 24, 1620 and references cited therein.
5. 3) Fleet, G.W.J.; Nicholas, S.I.; Smith, P.W.; Evans, S.V.; Fellows, L.E.; Nash, R.J. Tetrahedron Lett. 1985, 26, 3127 and references cited therein.
6. 4) Kim, Y J.; Kido. M.; Bando, M; Kitahara, T. Tetrahedron 1997, 53, 7501.
7. 5) Shibata, T.; Nakayama, O.; Tsurumi, Y; Okuhara, M.; Terano, H. and Kohsaka, M. J. Antibiot. 1988, 41, 296.
8. 6) For previous synthetic studies on the nectrisine 5, see, Chen, S.H.; Danishefsky, S.J. Tetrahedron Lett. 1990, 31, 2229.;
9. Kayakiri, H.; Nakamura, K.; Takase, S.; Setoi, H.; Uchida, I.; Terano, H.; Hashimoto, M.; Tada, T.; Koda, S. Chem. Pharm. Bull. 1991, 39, 2807.
10. 7) a) El-Ashmawy, A.E.; Horton, D. Carbohydr. Res. 1966, 3, 191.
11. b) Paulsen, H.; Propp, K.; Bruning J. Chem. Ber. 1969, 702, 469.
12. c) Paulsen, H.; Bruning, J.; Propp, K.; Heyns, K. Tetrahedron Lett. 1968, 8, 999.
13. 8) Kim, Y. J., Kitahara, T. Tetrahedron Lett. 1997, 38, 3423.
14. 9) Harusawa, S.; Hamada, Y; Shioiri, T. Tetrahedron Lett. 1979, 48, 4663.
15. 10) a) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 3337.
16. b) Kuwahara, S.; Moriguchi, M.; Miyagawa, K.; Konno, M.; Kodama, O. Tetrahedron 1995, 51, 8809 and references cited therein.
17. 11) Griffith, W.P.; Ley, S.V.; Whitcombe, G.P.; White, A.D. J. Chem. Soc., Chem. Commun. 1987, 1625.
18. 12) Kronenthal, D.R.; Han, C.Y.; Taylor, M.K. J. Org. Chem. 1982, 47, 2765.
19. 13) Naleway, J.J.; Raetz, C.R.H.; Anderson, L. Carbohydr. Res. 1988, 779, 199.
20. 14) For details of the biological evaluation, see, Tsujii, E.; Muroi, M.; Shiragami, N.; Takatsuki. A. Biochem. Biophys. Res. Commun. 1996, 220, 459.