A novel stereoselective route to a fumagillin and ovalicin synthetic intermediate

Tetrahedron Letters

Volumn 40, Issue 26, 1999, Pages 4797-4800

  Picoul, Willy ^a   Urchegui, Raquel ^a   Haudrechy, Arnaud ^a   Langlois, Yves ^a  

^a CNRS   (France)

Author keywords

Antitumour compounds; Metathesis; Rearrangement

Indexed keywords

ANTINEOPLASTIC AGENT; FUMAGILLIN; FUMAGILLOL CHLOROACETYLCARBAMATE; OVALICIN; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ANGIOGENESIS; ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; IMMUNOMODULATION; STEREOCHEMISTRY;

EID: 0033603553     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00912-0     Document Type: Article

References (27)

1. a) McCowen, M. C.; Calender, M. E.; Lawlis Jr, J. F. Science, 1951, 113, 202-203.
2. b) Tarbell, D. S.; Carman, R. M.; Chapman, D. D.; Cremer, S. E.; Cross, A. D.; Huffman, K. R.; Kunstmann, M.; McCorkindale, N. J.; McNally Jr, J. G.; Rosowsky, A.; Varino, F. H. L.; West, R. L. J. Am. Chem. Soc. 1961, 83, 3096-3113.
3. c) Turner, J.R.; Tarbell, J. R. Proc. Nat. Acad. Sci. U. S. 1962, 48, 733-735.
4. Bollinger, P.; Sigg, H. P.; Weber, H. P. Helv. Chim. Acta, 1973, 56, 819-830. and references cited therein.
5. Hatanaka, H.; Kino, T.; Hashimoto, M.; Tsurimi, Y.; Kuroda, A.; Tanaka, H.; Goto, T.; Okhura, M. J. Antibiot. 1988, 41, 999-1008.
6. For a review concerning low molecular weight compounds inhibitors of angiogenesis, see : Giannis, A.; Rübsam, F. Angew. Chem. Ed. Int. Engl. 1997, 36, 588-590.
7. Ingber, D.; Fujita, T.; Kishimoto, S.; Sudo, K.; Kanamaru, T.; Brem, H.; Folkman, J. Nature, 1990, 348, 555-557.
8. Corey, E. J.; Snider, B. B. J. Am. Chem. Soc. 1972, 94, 2549-2550.
9. Corey, E. J.; Dittami, J. P. J. Am. Chem. Soc. 1985, 107, 256-257.
10. Kim, D.; Ahn, S. K.; Bae, H.; Choi, W. J.; Kim, H. S. Tetrahedron Letters, 1997, 25, 4437-4440.
11. a) Corey, E. J. Guzman-Perez, A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 12109-12110.
12. b) Barton, D. H. R.; Bath, S.; Billington, D. C.; Géro, S. D.; Quiclet-Sire, B.; Samadi, M. J. Chem. Soc. Perkin Trans. 1, 1995, 1551-1558.
13. c) Barco, A.; Benetti, S.; De Risi, C.; Marchetti, P.; Pollini, G. P.; Zanirato, V. Tetrahedron : Asymmetry, 1998, 9, 2857-2864.
14. a) Amano, S.; Ogawa, N.; Ohtsuka, M.; Ogawa, S.; Chida, N. J. Chem. Soc. Chem. Commun. 1998, 1263-1264.
15. b) Amano, S.; Ogawa, N.; Ohtsuka, M.; Chida, N. Tetrahedron, 1999, 55, 2205-2224.
16. Marui, S.; Itoh, F.; Kozai, Y.; Sudo, K.; Kishimoto, S. Chem. Pharm. Bull. 1992, 40, 96-101.
17. b) Marui, S.; Kishimoto, S. Chem. Pharm. Bull. 1992, 40, 575-579.
18. c) Marui, S.; Yamamoto, T.; Sudo, K.; Akimoto, H.; Kishimoto, S. Chem. Pharm. Bull. 1995, 43, 588-593.
19. d) Turk, B. E.; Su, Z.; Liu, J. O. Bioorg. Med. Chem. 1998, 6, 1163-1169.
20. Büchi, G.; Powell Jr, J. E. J. Am. Chem. Soc. 1970, 92, 3126-3133.
21. The relatively cheap ethyl (S)-(-)-lactate was used for convenience. For the preparation of (-)-fumagillin, the enantiomeric ethyl lactate has to be used. See for example reference 8 and Zagalak, B.; Frey, P. A.; Karabatsos, G. L.; Abeles, R. H. J. Biol. Chem. 1966, 241, 3028-3035.
22. a) Ichikawa, Y.; Tsuboi, K.; Isobe, M. J. Chem. Soc. Perkin I, 1994, 2791-2796.
23. b) In this sequence of reactions the Masamune conditions (DBU, LiCl, THF) have been used for the Wittig reaction.
24. Macrichie, J. A.; Silcock, A.; Willis, C. L. Tetrahedron: Asymmetry, 1997,8, 3895-3902.
25. For a recent review concerning the asymmetric Claisen rearrangement, see : Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43-50.
26. 2, heptane-ether 20/1 to 12/1) and afforded 17a (920mg, 90%) as a pale yellow oil and 15 (10%).
27. For a recent example of preparation of functionalised cyclohexene by ring closure metathesis, see : Sellier, O.; Van De Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Letters, 1999, 40, 853-856 and references therein.