Total synthesis of amphidinolide J

Organic Letters

Volumn 10, Issue 20, 2008, Pages 4489-4492

  Barbazanges, Marion ^a   Meyer, Christophe ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIDINOLIDE J; CARBON; MACROLIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CARBON; MACROLIDES; MOLECULAR STRUCTURE;

EID: 58149145332     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801708x     Document Type: Article

References (35)

1. (a) Kobayashi, J.; Tsuda, M. Nat. Prod. Rep. 2004, 21, 77-93
2. (b) Kobayashi, J.; Kubota, T. J. Nat. Prod. 2007, 70, 451-460.
3. Kobayashi, J.; Sato, M.; Ishibashi, M. J. Org. Chem. 1993, 58, 2645-2646.
4. Ishibashi, M.; Takahashi, M.; Kobayashi, J. Tetrahedron 1997, 53, 7827-7832.
5. Williams, D. R.; Kissel, W. S. J. Am. Chem. Soc. 1998, 120, 11198-11199.
6. (a) Miyaura, N.; Suzuki. A. Chem. Rev. 1995, 95, 2457-2483.
7. (b) Chemler, S. R.; Trauner, D.; Danishefsky, S. Angew. Chem., Int. Ed. 2001, 40, 4544-4568.
8. Myers, A. G.; Yang, B. H.; Chen, H.; Mc Kinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511.
9. The diastereoselectivity, with respect to the newly formed stereo-center (C3), could not be accurately evaluated because of the presence of the THP and amide rotamers. The ee of trisylhydrazone 3 was later checked (ee > 90%) by supercritical fluid chromatography, see Supporting Information.
10. (a) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370.
11. (b) Cossy, J.; BouzBouz, S.; Hoveyda, A. H. J. Organomet. Chem. 2001, 634, 216-221.
12. (a) Hafner, A.; Duthaler, R. O.; Mari, R.; Rihs, J.; Rothe-Streit, P., Scharzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321-2336.
13. (b) Cossy, J.; BouzBouz, S.; Pradaux, F.; Willis, C; Bellosta, V. Synlett 1992, 1595-1606.
14. The ee of the homoallylic alcohol 7 was determined by supercritical fluid chromatography and comparison with a racemic sample prepared by addition of a crotylchromium reagent to aldehyde 6.
15. Andrus, M. B.; Lepore, S. D.; Sclafani, J. A. Tetrahedron Lett. 1997, 38, 4043-4046.
16. Français, A.; Bedel, O.; Haudrechy, A. Tetrahedron 2008, 64, 2495-2524.
17. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769-3772.
18. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885-888.
19. (a) Garegg, P. J.; Samuelsson, B. J. Chem. Soc., Perkin Trans, 1 1980, 2866-2869.
20. (b) Lange, G. L.; Gottardo, C. Synth. Commun. 1990. 20, 1473-1479.
21. Verkruijsse, H. D.; Heus-Kloos, Y. A.; Brandsma, L. J. Organomet. Chem. 1988, 338, 289-294.
22. Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R.J. Am. Chem. Soc. 1997, 119, 8738-8739.
23. For the ee determination, see Supporting Information.
24. (a) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, J. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889-3901.
25. (b) Burke, S. D.; Fobare, W. F.; Pacofsky, G. J. J. Org. Chem. 1983, 48, 5221-5228.
26. Hashimoto, N.; Aoyama, T.; Shioiri, T. Chem. Pharm. Bull. 1981, 29, 1475-1478.
27. Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461-5464.
28. (a) Marshall, J. A.; Schaaf, G. M. J. Org. Chem. 2003, 68, 7428-7432.
29. For a recent application of those conditions, see: (b) Corbu, A.; Aquino, M.; Pratap, T. V.; Retailleau, P.; Arseniyadis, S. Org. Lett. 2008, 10, 1787-1790.
30. An excess of alkynyllithium was used (2 equiv) and the terminal alkyne could be recovered (69% based on the unreacted reagent).
31. Similar reaction conditions as described in ref 4 were used but transacetylation could not be avoided.
32. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
33. For an example of translactonization from a 14- to a 15-membered ring, see: (a) Adachi, T. J. Org. Chem. 1989, 54, 3507-3510.
34. Translactonization of a 15- to a 13-membered ring has been observed, see: (b) Sarabia, F.; Chammaa, S. J. Org. Chem. 2005, 70, 7846-7857.
35. The reaction presumably proceeds under thermodynamic control but the use of longer reaction times resulted in the formation of byproducts presumably resulting from saponification, methanolysis, and/or degradation of the macrolactones.