Total synthesis of FR901483

Organic Letters

Volumn 3, Issue 5, 2001, Pages 765-767

  Ousmer, Malika ^a   Braun, Norbert A ^b   Ciufolini, Marco A ^a,b  

^a UNIVERSITÉ LYON 1   (France)

^b RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FR 901483; IMMUNOSUPPRESSIVE AGENT; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; CHEMISTRY; CYCLIZATION; FUNGUS; OXIDATION REDUCTION REACTION; SYNTHESIS;

CYCLIZATION; FUNGI; IMMUNOSUPPRESSIVE AGENTS; ORGANOPHOSPHORUS COMPOUNDS; OXIDATION-REDUCTION;

EID: 0035826326     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015526i     Document Type: Article

References (34)

1. Sakanioto, K.; Tsujii, E.; Abe, F.; Nakanishi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara, M. J. Antibiot. 1996, 49, 37.
2. Shirafuji, H.; Tsubotani, S.; Ishimaru, T.; Harada, S. Int. Patent PCT, 1991, WO91/13887.
3. FR901483. (a) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280 (synthetic studies).
4. (b) Bonjoch, J.; Diaba, F.; Puigbó, G.; Sole, D.; Segarra, V.; Santamaría, L.; Beleta, J.; Ryder, H.; Palacios, J.-M. Bioorg. Med. Chem. 1999, 7, 2891 (analogues).
5. (c) Snider, B. B.; Lin, H. J. Am. Chem. Soc. 1999, 121, 7778.
6. (d) Scheffler, G.; Seike, H.; Sorensen, E. J. Angew. Chem., Int. Ed. 2000, 39, 4593.
7. (e) Funk, R. L.; Maeng, J.-H. Abstracts of Papers. 220th National Meeting of the American Chemical Society, Washington, DC, August 20-24, 2000; American Chemical Society; Washington, DC, 2000; Abstract ORGN 264 (total synthesis). TAN1251A-D:
8. (f) Nagumo, S.; Nishida, A.; Yamazaki, C.; Murashige, K.; Kawahara, N. Tetrahedron Lett. 1998, 39, 4493.
9. (g) Snider, B. B.; Lin, H. Org. Lett. 2000, 2, 643 (total synthesis).
10. (a) Braun, N. A.; Ciufolini, M. A.; Peters, K.; Peters, E.-M. Tetrahedron Lett. 1998, 39, 4667.
11. (b) Braun, N. A.; Bray, J. D.; Ciufolini, M. A. Tetrahedron Lett. 1999, 40, 4985.
12. (c) Braun, N. A.; Ousmer, M.; Bray, J. D.; Bouchu, D.; Peters, K.; Peters, E.-M.; Ciufolini, M. A. J. Org. Chem. 2000, 65, 4397.
13. The preparation of 2 has been described: Abarbri, M.; Guignard, A.; Lamant, M. Helv. Chim. Acta 1995, 78, 109. Jung, M. E.; Jachiet, D.; Rohloff, J. R. Tetrahedron Lett. 1989, 30, 4211. Unfortunately, the product thus obtained is not optically pure. A short route to 2 that safeguards optical integrity was developed via (i) double methylation of phenolic and carboxy units of the N-carbomethoxy-L-tyrosine; (ii) LAH reduction of the ester; and (iii) carbamate cleavage. Details are provided as Supporting Information.
14. The preparation of 2 has been described: Abarbri, M.; Guignard, A.; Lamant, M. Helv. Chim. Acta 1995, 78, 109. Jung, M. E.; Jachiet, D.; Rohloff, J. R. Tetrahedron Lett. 1989, 30, 4211. Unfortunately, the product thus obtained is not optically pure. A short route to 2 that safeguards optical integrity was developed via (i) double methylation of phenolic and carboxy units of the N-carbomethoxy-L-tyrosine; (ii) LAH reduction of the ester; and (iii) carbamate cleavage. Details are provided as Supporting Information.
15. Fischer, E.; Lipschitz, W. Ber. Dtsch. Chem. Ges. 1915, 48, 360.
16. Vorbrüggen, H.; Krolikiewicz, K. Tetrahedron 1993, 49, 9353.
17. Ley, S. V.; Normand, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
18. (a) Myers, A. G.; Kung, D. W.; Zhong, B. J. Am. Chem. Soc. 2000, 722, 3236.
19. (b) Myers, A. G.; Zhong, B.; Kung, D. W.; Movassaghi, M.; Lanman, B. A.; Kwon, S. Org. Lett. 2000, 2, 3337.
20. (c) Myers, A. G.; Kung, D. W. Org. Lett. 2000, 2, 3019.
21. (d) Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828.
22. (e) Garner, P. Tetrahedron Lett. 1984, 25, 5855. See also ref 3d.
23. Structure confirmed by X-ray crystallography. Compound 13: Ousmer, M.; Braun, N. A.; Ciufolini, M. A.; Perrin, M. Z Kristallogr. NCS 2000, 215, 597. Compound 15: Ousmer, M.; Braun, N. A.; Ciufolini, M. A.; Perrin, M.; Bavoux, C. Z. Kristallogr. NCS. Submitted.
24. Structure confirmed by X-ray crystallography. Compound 13: Ousmer, M.; Braun, N. A.; Ciufolini, M. A.; Perrin, M. Z Kristallogr. NCS 2000, 215, 597. Compound 15: Ousmer, M.; Braun, N. A.; Ciufolini, M. A.; Perrin, M.; Bavoux, C. Z. Kristallogr. NCS. Submitted.
25. Brown, H. C.; Krishnamurthy, S. J. Am. Chem. Soc. 1972, 94, 7159.
26. (a) Yu, K.-L., Fraser-Reid, B. Tetrahedron Lett. 1998, 29, 979.
27. (b) Dreef, C. E.; Tuinman, R. J.; Elie, C. J. J.; van der Marel, G. A.; van Boom, J. H. Recl. Trav. Chim. Pays-Bas 1988, 107, 395.
28. The opportunities offered by such processes, in their manifold incarnations, are exemplified by the following: (a) Cox, C.; Danishefsky, S. J. Org. Lett. 2000, 2, 3493.
29. (b) Wipf, P.; Li, W. J. Org. Chem. 1999, 64, 4576.
30. (c) Kita, Y.; Egi, M.; Okajima, A.; Ohtsubo, M.; Takada, T.; Tohma, H. J. Chem. Soc., Chem. Commun. 1996, 1491.
31. (d) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106.
32. (e) Kita, Y.; Tohma, H.; Kikuchi, K.; Inagaki, M.; Yakura, T. J. Org. Chem. 1991, 56, 435.
33. (f) Tamura, Y.; Yakura, T.; Haruta, J.-I.; Kita, Y. J. Org. Chem. 1987, 52, 3927.
34. (g) Corey, E. J.; Dittami, J. P. J. Am. Chem. Soc. 1985, 107, 256.