Total synthesis of sphingofungin F

Synlett

Volumn , Issue 18, 2006, Pages 2985-2988

  Li, Min ^a   Wu, Anmei ^b  

^a GEORGETOWN UNIVERSITY MEDICAL CENTER   (United States)

^b Orgchem Technologies Inc   (United States)

Author keywords

L quebrachitol; Michael addition; Sphingofungin F; Total synthesis; Wittig type reaction

Indexed keywords

ANTIFUNGAL AGENT; METHYLSULFONATE; SPHINGOFUNGIN F; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; MICHAEL ADDITION; STEREOCHEMISTRY; WITTIG REACTION;

EID: 33751258904     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-947333     Document Type: Article

References (57)

1. For reviews, see: (a) Hakomori, S. In Sphingolipid Biochemistry. Handbook of Lipid Research, Vol. 3; Kafner, J. N.; Hakomori, S., Eds.; Plenum: New York, 1983, 1.
2. (b) Merrill, A. H. Jr.; Sweeley, C. C. In Biochemistry of Lipids, Lipoproteins and Membranes; Vance, D. E.; Vance, J., Eds.; Elsevier Science B. V.: Amsterdam, 1996, 309.
3. (c) Hannun, Y. A. Sphingolipid-Mediated Signal Transduction; Chapman and Hall: New York NY, 1997.
4. (d) Hannum, Y. A. Science 1996, 274, 1855.
5. (e) Spiegel, S.; Milstein, S. J. Membr. Biol. 1995, 146, 225.
6. (f) Shayman, J. A. J. Am. Soc. Nephrol. 1996, 7, 171.
7. (g) Igarashi, Y. J. Biochem. (Tokyo) 1997, 122, 1080.
8. (h) Ariga, T.; Jarvis, W. D.; Yu, R. K. J. Lipid. Res. 1998, 39, 1.
9. (a) Hannun, Y. A.; Loomis, C. R.; Merrill, A. H.; Bell, R. M. J. Biol. Chem. 1986, 261, 2604.
10. (b) Hannun, Y. A. Science 1989, 243, 500.
11. (a) Nugent, T. C.; Hudlicky, T. J. Org. Chem. 1998, 63, 510.
12. (b) Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Kanada, K. J. Am. Chem. Soc. 1998, 120, 908.
13. (c) Mandala, S. M.; Harris, G. H. Methods Enzymol. 2000, 311, 335.
14. (a) VanMiddlesworth, F.; Dufresne, C.; Wincott, F. E.; Mosley, R. T.; Wilson, K. E. Tetrahedron Lett. 1992, 33, 297.
15. (b) VanMiddlesworth, F.; Giacobbe, R. A.; Lopez, M.; Garrity, G.; Bland, J. A.; Bartizal, K.; Fromtling, R. A.; Polishook, J.; Zweerink, M.; Edison, A. M.; Rozdilsky, W.; Wilson, K. E.; Monaghan, R. L. J. Antibiot. 1992, 45, 861.
16. (c) Horn, W. S.; Smith, J. L.; Bills, G. F.; Raghoobar, S. L.; Helms, G. L.; Kurtz, M. B.; Marrinan, J. A.; Frommer, B. R.; Thornton, R. A.; Mandala, S. M. J. Antibiot. 1992, 45, 1692.
17. (a) Fujita, T.; Inoue, K.; Yamamoto, S.; Ikumoto, T.; Sasaki, S.; Toyoma, R.; Yoneta, M.; Hoshino, Y.; Okumoto, T. J. Antibiot. 1994, 47, 208.
18. (b) Miyake, Y.; Kozutsumi, Y.; Nakamura, S.; Fujita, T.; Kawasaki, T. Biochem. Biophys. Res. Commun. 1995, 211, 396.
19. (c) For synthesis of myriocin, see: Oishi, T.; Ando, K.; Chida, N. Chem. Commun. 2001, 1932; and references cited therein.
20. Zweerink, M. M.; Edison, A. M.; Wells, G. B.; Pinto, W.; Lester, R. L. J. Biol. Chem. 1992, 267, 25032; and references cited therein.
21. (a) Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 2001, 123, 12191.
22. (b) Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818.
23. (a) Wang, B.; Yu, X.-M.; Lin, G.-Q. Synlett 2001, 904.
24. (b) Liu, D.-G.; Wang, B.; Lin, G.-Q. J. Org. Chem. 2000, 65, 9114.
25. (a) Nakamura, T.; Shiozaki, M. Tetrahedron 2002, 58, 8779.
26. (b) Nakamura, T.; Shiozaki, M. Tetrahedron Lett. 2001, 42, 2701.
27. Oishi, T.; Ando, K.; Inomiya, K.; Sato, H.; Iida, M.; Chida, N. Org. Lett. 2002, 4, 151.
28. (a) Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Kanada, K. J. Am. Chem. Soc. 1998, 120, 908.
29. (b) Kobayashi, S.; Furuta, T. Tetrahedron 1998, 54, 10275.
30. Lee, K.-Y.; Oh, C.-Y.; Ham, W.-H. Org. Lett. 2001, 4, 4403.
31. (a) Sano, S.; Kobayashi, Y.; Kondo, T.; Takebayashi, M.; Maruyama, S.; Fujita, T.; Nagao, Y. Tetrahedron Lett. 1995, 36, 2097.
32. (b) Payette, D. R.; Just, G. Can. J. Chem. 1981, 59, 269.
33. The following reference provides detailed procedures for both the preparation of precursors of both 8 and its regioisomer, and the preparation of the regioisomer of compound 8 from the corresponding precursor. It should be mentioned that the synthesis of 8 was accomplished from its corresponding precursor following the same procedure. See: Qiao, L.; Hu, Y.; Nan, F.; Powis, G.; Kozikowski, A. P. Org. Lett. 2000, 2, 115.
34. For recent examples of Wittig and Horner-Wadsworth-Emmons reaction, see: (a) List, B.; Doehring, A.; Fonseca, M. T. H.; Job, A.; Torres, R. R. Tetrahedron 2006, 62, 476.
35. For reviews, see: (b) Harvey, R. G. Curr. Org. Chem. 2004, 8, 303.
36. (c) Quan, L.-G.; Cha, J.-K. Chem. Phys. Lipids 2004, 128.
37. (d) Rein, T.; Vares, L.; Kawasaki, I.; Pedersen, T. M.; Norrby, P.-O.; Brandt, P.; Tanner, D. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 144-146, 169.
38. (a) Cardillo, G.; Simone, A. D.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051.
39. (b) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670.
40. (c) Krawczyk, H. Synth. Commun. 2000, 30, 1787.
41. (a) Paulsen, H.; Heiker, F. R. Angew Chem., Int. Ed. Engl. 1980, 19, 904.
42. (b) Paulsen, H.; Heiker, F. R. Liebigs Ann. Chem. 1981, 2180.
43. Bartlett, P. A.; Johnson, W. S. Tetrahedron Lett. 1970, 4459.
44. For recent examples of Barton decarboxylation, see: (a) Masterson, D. S.; Porter, N. A. Org. Lett. 2002, 4, 4253.
45. (b) Elena, M.; Taddei, M. Tetrahedron Lett. 2001, 42, 3519.
46. (c) For a review, see: Barton, D. H. R. Aldrichimica Acta 1990, 23, 3.
47. (a) Gigg, J.; Gigg, R.; Payne, S.; Conant, R. J. Chem. Soc., Perkin. Trans. 1 1987, 423.
48. (b) Vacca, J. P.; de Solms, S. J.; Huff, J. R. J. Am. Chem. Soc. 1987, 109, 3478.
49. (c) Vacca, J. P.; de Solms, S. J.; Huff, J. R.; Billington, B. C.; Baker, R.; Kulagowski, J. J.; Mawer, I. M. Tetrahedron 1989, 45, 5679.
50. 3): δ = 166.68, 166.50, 159.31, 159.16, 157.35, 138.56, 138.45, 135.46, 135.15, 134.43, 133.10, 131.58, 131.38, 130.73, 129.89, 129.50, 128.55, 128.38, 128.37, 128.00, 127.99, 113.91, 110.89, 83.22, 81.49, 81.28, 76.50, 75.60, 71.73, 69.19, 55.63, 27.35, 25.91.
51. (a) Bredenkamp, M. W.; Holzapfel, C. W.; Swanepoel, A. D. Tetrahedron Lett. 1990, 31, 2759.
52. (b) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643.
53. (c) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987, 261.
54. 9: 679.2781; found: 679.2785.
55. (a) Chida, N.; Yamada, L.; Suzuki, M.; Ogawa, S. J. Carbohydr. Chem. 1992, 11, 137.
56. (b) Paulsen, H.; Roeben, W. Liebigs Ann. Chem. 1985, 5, 974.
57. 3OD): δ = 214.53, 175.32, 135.75, 130.30, 76.25, 75.73, 72.44, 67.03, 43.50, 33.52, 32.79, 30.26, 30.03,25.02, 23.67, 21.80, 14.43.