Synthesis of a prenylated and immunosuppressive marine galactosphingolipid with cyclopropane-containing alkyl chains: (2S,3R,11S,12R,2‴R,5‴Z,11‴S,12‴R)-plakoside a and its (2S,3R,11R,12S,2‴R,5‴Z,11‴R,12‴S)isomer

European Journal of Organic Chemistry

Volumn , Issue 20, 2001, Pages 3797-3809

  Seki, Masanori ^a   Mori, Kenji ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Asymmetric synthesis; Cerebrosides; Immunochemistry; Natural products; Total synthesis

Indexed keywords

CYCLOPROPANE; GLYCOSPHINGOLIPID; IMMUNOSUPPRESSIVE AGENT; PLAKOSIDE A; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; IMMUNOSUPPRESSIVE TREATMENT;

EID: 0034770155     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200110)2001:20<3797::AID-EJOC3797>3.0.CO;2-Y     Document Type: Article

References (21)

1. V. Costantino, E. Fattorusso, A. Mangoni, M. Di Rosa, A. Ianaro, J. Am. Chem. Soc. 1997, 119, 12465-12470.
2. V. Costantino, E. Fattorusso, A. Mangoni, Tetrahedron 2000, 56, 5953-5957.
3. M. Seki, A. Kayo, K. Mori, Tetrahedron Lett. 2001, 42, 2357-2360.
4. K. C. Nicolaou, J. Li, G. Zenke, Helv. Chim. Acta 2000, 83, 1977-2006.
5. K. Laumen, M. Schneider, Tetrahedron Lett. 1985, 26, 2073-2076.
6. W. Kasel, P. G. Hultin, J. B. Jones, J. Chem. Soc., Chem. Commun. 1985, 1563-1564.
7. D. Grandjean, P. Pale, J. Chuche, Tetrahedron 1991, 47, 1215-1230.
8. C. Fouquet, M. Schlosser, Angew. Chem. Int. Ed. Engl. 1974, 13, 82-83.
9. P. Garner, J. M. Park, E. Malecki, J. Org. Chem. 1988, 53, 4395-4398.
10. T. Fujisawa, M. Nagai, Y. Koike, M. Shimizu, J. Org. Chem. 1994, 59, 5865-5867.
11. K. Mori, T. Takigawa, T. Matsuo, Tetrahedron 1979, 35, 933-940.
12. A. G. Cole, J. Wilkie, D. Gani, J. Chem. Soc., Perkin Trans. 1 1995, 2695-2707.
13. G. J. F. Chittenden, Carbohydr. Res. 1988, 183, 140-143.
14. M. Izumi, O. Turuta, S. Harayama, H. Hashimoto, J. Org. Chem. 1997, 62, 992-998.
15. U. E. Udodong, C. S. Rao, B. Fraser-Reid, Tetrahedron 1992, 48, 4713-4724.
16. C. Li, L.-D. Nord, P. B. Savage, Am. Chem. Soc., Division of Org. Chem., Abstracts: 219th ACS Meeting, San Francisco, March 26-30, 2000, No. 485.
17. A. Yajima, H. Takikawa, K. Mori, Liebigs Ann. 1996, 1083-1089.
18. K. Mori, J. Heterocycl. Chem. 1996, 33, 1497-1517.
19. H. Takikawa, T. Maeda, M. Seki, H. Koshino, K. Mori, J. Chem. Soc., Perkin Trans. 1 1997, 97-111.
20. K. Otaka, K. Mori, Eur. J. Org. Chem. 1999, 1795-1802.
21. 13C NMR spectra of Plakoside A (1)] is available; see footnote first page.