Synthesis of a promising immunosuppressant: FR252921

Organic Letters

Volumn 9, Issue 23, 2007, Pages 4761-4764

  Amans, Dominique ^a   Bellosta, Véronique ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; AMINE; CARBOXYLIC ACID; ESTER; FR 252921; IMMUNOSUPPRESSIVE AGENT; LACTAM; LACTONE; STANNANE; TIN DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOMERISM; SYNTHESIS;

ACIDS; AMINES; CARBOXYLIC ACIDS; ESTERS; IMMUNOSUPPRESSIVE AGENTS; ISOMERISM; LACTAMS; LACTONES; MOLECULAR STRUCTURE; TIN COMPOUNDS; VINYL COMPOUNDS;

EID: 36348930021     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702110k     Document Type: Article

References (31)

1. (a) Fujine, K.; Tanaka, M.; Ohsumi, K.; Hashimoto, M.; Takase, S.; Ueda, H.; Hino, M.; Fujii, T. J. Antibiot. 2003, 56, 55-61.
2. (b) Fujine, K.; Abe, F.; Seki, N.; Ueda, H.; Hino, M.; Fujii, T. J. Antibiot. 2003, 56, 62-67.
3. (c) Fujine, K.; Ueda, H.; Hino, M.; Fujii, T. J. Antibiot. 2003, 56, 68-71.
4. Pohanka, A.; Broberg, A.; Johansson, M.; Kenne, L.; Levenfors, J. J. Nat. Prod. 2005, 68, 1380-1385.
5. Yu, S.; Liu, F.; Ma, D. Tetrahedron Lett. 2006, 47, 9155-9157.
6. Falck, J. R.; He, A.; Fukui, H.; Tsutsui, H.; Radha, A. Angew. Chem., Int. Ed. 2007, 46, 4527-4529.
7. (a) Amans, D.; Bellosta, V.; Cossy, J. Angew. Chem., Int. Ed. 2006, 45, 5870-5874 and references therein.
8. (b) Amans, D.; Le Flohic, A.; Bellosta, V.; Meyer, C.; Cossy, J. Pure Appl. Chem. 2007, 79, 677-684.
9. Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, J.; Rhote-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321-2336.
10. Sakaitani, M.; Ohfune, Y. Tetrahedron Lett. 1985, 26, 5543-5546.
11. Huang, Z.; Negishi, E. Org. Lett. 2006, 8, 3675-3678.
12. Vinyl iodide 12 was obtained by performing a zirconium-assisted carboalumination of propargyl alcohol according to: Negishi, E.; Van Horn, D. E.; King, A. O.; Okukado, N. Synthesis 1979, 501-502.
13. 1H NMR spectra of the two corresponding mandelates, following the procedure described by: Seco, J. M.; Quiñoa, E.; Riguera, R. Tetrahedron: Asymmetry 2001, 12, 2915-2925.
14. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
15. (b) Betzer, J.-F.; Lallemand, J.-L.; Pancrazi, A. Synthesis 1998, 522-534.
16. (c) Nicolaou, K. C.; Li, Y.; Sugita, K.; Monenschein, H.; Guntupalli, P.; Mitchell, H. J.; Fylaktakidou, K. C.; Vourloumis, D.; Giannakakou, P.; O'Brate, A. J. Am. Chem. Soc. 2003, 125, 15443-15454.
17. (a) Riediker, M.; Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1989, 28, 494-495.
18. (b) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 495-497.
19. (c) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832.
20. (d) Duthaler, R. O.; Herold, P.; Wyler-Helfer, S.; Riediker, M. Helv. Chim. Acta 1990, 73, 659-673.
21. 1H NMR spectra of the two corresponding mandelates; see ref 10.
22. Many unsuccessful procedures were attempted according to: (a) Trost, B. M.; Chisholm, J. D. Org. Lett. 2002, 4, 3743-3745.
23. (b) Hikota, M.; Sakurai, Y.; Horita, K.; Yonemitsu, O. Tetrahedron Lett. 1990, 31, 636-6370.
24. (c) Mitsunobu, O. Synthesis 1981, 1-28.
25. For a review on macrolactonizations, see: Parenty, A.; Moreau, X.; Campagne, J.-M. Chem. Rev. 2006, 106, 911-939.
26. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
27. 2 are also consistent with the (2Z,4E,6E,12R,13R, 18R) isomer and not the (2E,4E,6E,12R, 13R,18R) stereoisomer as reported.
28. 1H spectrum that they provided to us made at a different concentration. However, the optical rotation for our seco-acid was absolutely identical to the one reported by Falck. See experimental section for spectra.
29. (a) Shiina, I.; Kubota, M.; Ibuka, R. Tetrahedron Lett. 2002, 43, 7535-7539.
30. (b) Shiina, I.; Kubota. M.; Oshiumi, H.; Hashizume, M. J. Org. Chem. 2004, 69, 1822-1830.
31. Under the same conditions, Falck et al. have isolated FR252921 in 10% yield by reverse phase chromatography.