Total synthesis of agelagalastatin

Organic Letters

Volumn 8, Issue 18, 2006, Pages 3971-3974

  Lee, Yong Joo ^a   Lee, Bo Young ^a   Jeon, Heung Bae ^a   Kim, Kwan Soo ^a  

^a Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AGELAGALASTATIN; ANTINEOPLASTIC AGENT; GLYCOSPHINGOLIPID;

AGELAS; ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AGELAS; ANIMALS; ANTINEOPLASTIC AGENTS; MOLECULAR STRUCTURE; NEUTRAL GLYCOSPHINGOLIPIDS;

EID: 33748947321     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061444o     Document Type: Article

References (30)

1. Pettit, G. R.; Xu, J.-p.; Gingrich, D. E.; Williams, M. D.; Doubek, D. L.; Chapius, J.-C.; Schmidt, J. M. Chem. Commun. 1999, 915.
2. Natori, T.; Morita, M.; Akimoto, K.; Koezuka, Y. Tetrahedron 1994, 50, 2771.
3. Cafieri, F.; Fattorusso, E.; Mahajnah, Y.; Mangoni, A. Leibigs Ann. Chem. 1994, 1187.
4. Costantino, V.; Fattorusso, E.; Mangoni, A.; Aknin, M.; Gaydon, E. M. Leibigs Ann. Chem. 1994, 1181.
5. Costantino, V.; Fattorusso, E.; Mangoni, A. Tetrahedron 1996, 52, 1573.
6. D'Ambrosio, M.; Ripamonti, M.; Debitus, C.; Waikedre, J.; Pietra, F. Helv. Chim. Acta 1996, 79, 727.
7. Motoki, K.; Kobayashi, E.; Uchida, T.; Fukushima, H.; Koezuka, Y. Bioorg. Med. Chem. Lett. 1995, 5, 705.
8. Crul, M.; Mathôt, R. A. A.; Giaccone, G.; Punt, C. J. A.; Rosing, H.; Hillebrand, M. J. X.; Ando, Y.; Nishi, N.; Tanaka, H.; Schellens, J. H. M.; Beijnen, J. H. Cancer Chemother. Pharmacol. 2002, 49, 287.
9. Jansson, P.-E.; Lindberg, B. Carbohydr. Res. 1980, 82, 97.
10. McConville, M. J.; Homans, S. W.; Thomas-Oates, J. E.; Dell, A.; Bacic, A. J. Biol. Chem. 1990, 265, 7385.
11. Parra, E.; Jiménez-Barbero, J.; Bernabé, M.; Leal, J. A.; Prieto, A.; Gómez-Miranda, B. Carbohydr. Res. 1994, 251, 315.
12. For a review on 1,2-cis-glycosylation, see: Demchenko, A. V. Synlett 2003, 1225.
13. Gelin, M.; Ferriéres, V.; Plusquellec, D. Carbohydr. Lett. 1997, 2, 381.
14. Gelin, M.; Ferriéres, V.; Plusquellec, D. Eur. J. Org. Chem. 2000, 1423.
15. (a) Kim, K. S.; Kim, J. H.; Lee, Y. J.; Lee, Y. J.; Park, J. J. Am. Chem. Soc. 2001, 123, 8477.
16. (b) Kim, K. S.; Park, J.; Lee, Y. J.; Seo, Y. S. Angew. Chem., Int. Ed. 2003, 42, 459.
17. (c) Kim, K. S.; Kang, S. S.; Seo, Y. S.; Kim, H. J.; Lee, Y. J.; Jeong, K.-S. Synlett 2003, 1311.
18. (d) Kwon, Y. T.; Lee, Y. J.; Lee, K.; Kim, K. S. Org. Lett. 2004, 6, 3901.
19. (e) Lee, Y. J.; Lee, K.; Jung, E. H.; Jeon, H. B.; Kim, K. S. Org. Lett. 2005, 7, 3263.
20. ( 16) Ferriéres, V.; Gelin, M.; Boulch, R.; Toupet, L.; Plusquellec, D. Carbohydr. Res. 1998, 314, 79.
21. (a) Torssell, S.; Somfai, P. Org. Biomol. Chem. 2004, 2, 1643.
22. (b) Rai, A. N.; Basu, A. Org. Lett. 2004, 6, 2861.
23. (c) Rai, A. N.; Basu, A. J. Org. Chem. 2005, 70, 8228.
24. (d) Chaudhari, V. D.; Ajish Kumar, K. S.; Dhavale, D. D. Org. Lett. 2005, 7, 5805.
25. Cheng, X.; Khan, N.; Mootoo, D. R. J. Org. Chem. 2000, 65, 2544.
26. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
27. Tuch, A.; Saniére, M.; Merrer, Y. L.; Depezay, J.-C. Tetrahedron: Asymmetry 1996, 7, 897.
28. Belleau, B.; Malek, G. J. Am. Chem. Soc. 1968, 90, 1651.
29. 4 as the promoter for glycosyl fluoride, see: Mukaiyama, T.; Murai, Y.; Shoda, S. Chem. Lett. 1981, 431.
30. See the Supporting Information.