Efficient syntheses of pterulone, pterulone B and related analogues

Organic and Biomolecular Chemistry

Volumn 1, Issue 23, 2003, Pages 4209-4219

  Lemaire, Philippe ^a   Balme, Geneviève ^a   Desbordes, Philippe ^b   Vors, Jean Pierre ^b  

^a UNIVERSITÉ LYON 1   (France)

^b BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ALKYLATION; DRUG PRODUCTS; FUNGI; METABOLITES; MOLECULAR STRUCTURE; PHASE TRANSITIONS; SYNTHESIS (CHEMICAL);

INTRAMOLECULAR WITTIG REACTION; PHYTOPATHOGENIC FUNGI; PTERULONE; RING CLOSING METATHESIS; UNNATURAL ANALOGUES;

ANTIBIOTICS;

FUNGI;

ALCOHOL DERIVATIVE; ANTIFUNGAL AGENT; BENZOFURAN DERIVATIVE; OXEPINE DERIVATIVE; PHENOL; PTERULONE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; FUNGUS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALCOHOLS; ALKYLATION; ANTIFUNGAL AGENTS; BENZOFURANS; FUNGI; MOLECULAR STRUCTURE; OXEPINS; PHENOL; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0347410691     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b306356a     Document Type: Article

References (49)

1. M. Engler, T. Anke and O. Sterner, J. Antibiot., 1997, 50, 330-333.
2. M. Engler, T. Anke and O. Sterner, Z. Naturforsch., 1998, 53c, 318-324.
3. M. Engler, T. Anke, O. Sterner and U. Brandt, J. Antibiot., 1997, 50, 325-329.
4. J. B. P. A. Wijnberg, A. Van Veldhuizen, H. J. Swartz, J. C., Frankland and J. A. Field, Tetrahedron Lett., 1999, 40, 5767-5770.
5. B. W. T. Gruijters, A. Van Veldhuizen, C. A. G. M. Weijers and J. B. P. A. Wijnberg, J. Nat. Prod., 2002, 65, 558-561
6. P. Kahnberg, C. W. Lee, R. H. Grubbs and O. Sterner, Tetrahedron, 2002, 58, 5203-5208
7. P. Kahnberg and O. Sterner, Tetrahedron, 2001, 57, 7181-7184.
8. S.-T. Huang, H.-S. Kuo and C.-T. Chen, Tetrahedron Lett., 2001, 42, 7473-7475.
9. G. Balme, I. Coudanne, P. Desbordes, N. Huser, P. Lemaire, A. Mousques, A. Nivlet and J.-P. Vors, PCT Int. Appl. WO 0314104 (priority date: 8th August 2001).
10. For reviews on the chemistry of sulfones: The Chemistry of sulfones and sulfoxides, Eds S. Patai, Z. Rappoport and C. Stirling, J. Wiley & Sons, New York, 1988
11. B. M. Trost, Bull. Chem. Soc. Jpn., 1988, 61, 107-124
12. N. S. Simpkins, Sulfones in Organic Synthesis, Pergamon Press, Oxford, 1993
13. The Synthesis of Sulfones, Sulfoxides and Cyclic Sulfides, Eds S. Patai and Z. Rappoport, Wiley & Sons, New York, 1994
14. C. M. Rayner, Contemp. Org. Synth., 1994, 1, 191-203
15. C. M. Rayner, Contemp. Org. Synth., 1995, 2, 409-440
16. C. M. Rayner, Contemp. Org. Synth., 1996, 3, 499-533
17. R. Chinchilla and C. Nájera, Recent Res. Dev. Org. Chem., 1997, 1, 437
18. Nájera and J. M. Sansano, Recent Res. Dev. Org. Chem., 1998, 2, 637-683
19. C. Nájera and M. Yus, Tetrahedron, 1999, 55, 10547-10658
20. E. N. Prilezhaeva, Russ. Chem. Rev., 2000, 69, 367-408.
21. C. Kaiser, M. S. Schwartz, D. F. Coella and J. R. Wardwell, J. Med. Chem., 1975, 18, 674-683 (sodium benzenesulfinate was used instead of magnesium toluenesulfinate).
22. J.C. Carretero, R. G. Arrayas and I. S. De Gracia, Tetrahedron Lett., 1997, 38, 8537-8539
23. J. C. Carretero and R. G. Arrayas, J. Org. Chem., 1998, 63, 2993-3005.
24. Z.-M. Wang, X.-L. Zhang and K. B. Sharpless, Tetrahedron Lett., 1993, 34, 2267-2270.
25. V. I. Levashova, V. A. Krasnova and L. I. Bunina-Krivorukova, Zh. Org. Khim., 1989, 25, 1463-1465.
26. H. Tsuda, Y. Takemura, Y. Suzuki and T. Kato, Heterocycles, 1997, 44, 139
27. S. Czernecki, C. Georgoulis and C. Provelenghiou, Tetrahedron Lett., 1976, 39, 3535.
28. G. A. Molander, Acc. Chem. Res, 1998, 39, 603-610.
29. S. Hanessian, L. D. Cantin and D. Andreotti, J. Org. Chem., 1999, 64, 4893-4900.
30. G. Guillena and C. Nájera, J. Org. Chem., 2000, 65, 7310-7322
31. M. Kanai, A. Muraoka, T. Tanaka, M. Sawada, N. Ikota and K. Tomiaka, Tetrahedron, 1995, 51, 9349-9352.
32. B. M. Trost, P. Seoane, S. Mignani and M. Acemoglu, J. Am. Chem. Soc., 1989, 111, 7492.
33. Z. Song and P. Beak, J. Am. Chem. Soc., 1990, 112, 8126-8134.
34. E. N. Jacobsen, L. Deng, Y. Furakawa and L. E. Martinez, Tetrahedron, 1994, 50, 4332.
35. J.-T. Zhang, W. Dai and R. G. Harvet, J. Org. Chem., 1998, 63, 8125-8132.
36. Wittig reaction products resulting from aromatic aldehydes are generally obtained as an E-Z-olefinic mixture: H. O. House, V. K. Jones and J. Frank, J. Org. Chem, 1964, 29, 3327
37. B. E. Maryanoff and A. B. Reitz, Chem. Rev., 1989, 89, 863-927.
38. W. P. Griffith, S. V. Ley, G. P. Whitcombe and A. D. White, J. Chem. Soc., Chem. Commun., 1987, 1625-1627
39. W. P. Griffith and S. V. Ley, Adrichim. Acta, 1990, 23, No. 1
40. S. V. Ley, J. Norman, W. P. Griffith and S. P. Marsden, Synthesis, 1994, 639-665.
41. G. Carr, C. Dean and D. Whittaker, J. Chem. Soc., Perkin Trans. 2, 1989, 71-76
42. J. A. Findlay, W. D. MacKay and W. S. Bowers, J. Chem. Soc (C), 1970, 2631-2635.
43. M. A. Ali and Y. Tsuda, Chem. Pharm. Bull., 1992, 40, 2842
44. S. H. Reich, M. Melnick, M. J. Pino, M. A. M. Fuhry, A. J. Trippe, K. Appelt, J. F. Davies II, B. W. Wu and L. Musick, J. Med. Chem., 1996, 39, 2781-2794.
45. Attempts to isomerise in a single operation led generally to decomposition of the material and resulted at best in only modest yields of the expected product.
46. J. Yu, M. J. Gaunt and J. B. Spencer, J. Org. Chem., 2002, 67, 4627-4629.
47. This alkylation reaction did not proceed in the absence of DBU.
48. When the reductive desulfonylation was carried out in the presence of less than 6 equimolar amounts of sodium amalgam, a significant amount of the starting material was recovered along with a mixture of 30 and 31.
49. P. H. J. Carlsen, T. Katsuki, V. S. Martin and K. B. Sharpless, J. Org. Chem., 1981, 46, 3936-3938.