Ti-catalyzed transannular cyclization of epoxygermacrolides. Synthesis of antifungal (+)-tuberiferine and (+)-dehydrobrachylaenolide

Tetrahedron

Volumn 64, Issue 52, 2008, Pages 11938-11943

  Justicia, José ^a   de Cienfuegos, Luis Álvarez ^a   Estévez, Rosa E ^a   Paradas, Miguel ^a   Lasanta, Ana M ^a   Oller, Juan L ^a   Rosales, Antonio ^a   Cuerva, Juan M ^a   Oltra, J Enrique ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

(+) COSTUNOLIDE; (+) DEHYDROBRACHYLAENOLIDE; (+) TUBERIFERINE; 1,4 EPOXYGERMACROLIDE; AMPHOTERICIN B; EUDESMANOLIDE DERIVATIVE; HYDROGEN; MACROLIDE; TITANIUM; UNCLASSIFIED DRUG; WATER;

ANTIFUNGAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PHYCOMYCETES; PRIORITY JOURNAL;

PHYCOMYCES BLAKESLEEANUS;

EID: 56249123930     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.08.114     Document Type: Article

References (56)

1. Nugent W.A., and RajanBabu T.V. J. Am. Chem. Soc. 110 (1988) 8561-8562
2. RajanBabu T.V., and Nugent W.A. J. Am. Chem. Soc. 111 (1989) 4525-4527
3. RajanBabu T.V., Nugent W.A., and Beattie M.S. J. Am. Chem. Soc. 112 (1990) 6408-6409
4. RajanBabu T.V., and Nugent W.A. J. Am. Chem. Soc. 116 (1994) 986-997
5. 2, see:
6. Enemærke R.J., Larsen J., Skrydstrup T., and Daasbjerg K. J. Am. Chem. Soc. 126 (2004) 7853-7864
7. Daasbjerg K., Svith H., Grimme S., Gerenkamp M., Mück-Lichtenfeld C., Gansäuer A., Barchuck A., and Keller F. Angew. Chem., Int. Ed 45 (2006) 2041-2044
8. 2TiCl
9. For pertinent reviews, see:
10. Gansäuer A., and Bluhm H. Chem. Rev. 100 (2000) 2771-2788
11. Gansäuer A., and Pierobon M. In: Renaud P., and Sibi M.P. (Eds). Radicals in Organic Synthesis Vol. 2 (2001), Wiley-VCH, Weinheim, Germany 207-220
12. Gansäuer A., and Rinker B. Tetrahedron 58 (2002) 7017-7026
13. Gansäuer A., and Narayan S. Adv. Synth. Catal. 344 (2002) 465-475
14. Gansäuer A., and Rinker B. In: Marek I. (Ed). Titanium and Zirconium in Organic Synthesis (2002), Wiley-VCH, Weinheim, Germany 435-450
15. Gansäuer A., Lauterbach T., and Narayan S. Angew. Chem., Int. Ed. 42 (2003) 5556-5573
16. Cuerva J.M., Justicia J., Oller-López J.L., Bazdi B., and Oltra J.E. Mini-Rev. Org. Chem. 3 (2006) 23-35
17. Cuerva J.M., Justicia J., Oller-López J.L., and Oltra J.E. Top. Curr. Chem. 264 (2006) 63-91
18. Gansäuer A., and Bluhm H. Chem. Commun. (1998) 2143-2144
19. Gansäuer A., Pierobon M., and Bluhm H. Angew. Chem., Int. Ed. 37 (1998) 101-103
20. Gansäuer A., Bluhm H., and Pierobon M. J. Am. Chem. Soc. 120 (1998) 12849-12859
21. Barrero A.F., Rosales A., Cuerva J.M., and Oltra J.E. Org. Lett. 5 (2003) 1935-1938
22. Justicia J., Oller-López J.L., Campaña A.G., Oltra J.E., Cuerva J.M., Buñuel E., and Cárdenas D.J. J. Am. Chem. Soc. 127 (2005) 14911-14921
23. Justicia J., Oltra J.E., Barrero A.F., Guadaño A., González-Coloma A., and Cuerva J.M. Eur. J. Org. Chem. (2005) 712-718
24. Justicia J., Campaña A.G., Bazdi B., Robles R., Cuerva J.M., and Oltra J.E. Adv. Synth. Catal. 350 (2008) 571-576
25. Justicia J., Rosales A., Buñuel E., Oller-López J.L., Valdivia M., Haidour A., Oltra J.E., Barrero A.F., Cárdenas D.J., and Cuerva J.M. Chem.-Eur. J. 10 (2004) 1778-1788
26. Justicia J., Oltra J.E., and Cuerva J.M. Tetrahedron Lett. 45 (2004) 4293-4296
27. Justicia J., Oltra J.E., and Cuerva J.M. J. Org. Chem. 70 (2005) 8265-8270
28. Gansäuer A., Worgull D., and Justicia J. Synthesis (2006) 2151-2154
29. Gansäuer A., Justicia J., Rosales A., Worgull D., Rinker B., Cuerva J.M., and Oltra J.E. Eur. J. Org. Chem. (2006) 4115-4127
30. Barrero A.F., Cuerva J.M., Álvarez-Manzaneda E.J., Oltra J.E., and Chahboun R. Tetrahedron Lett. 43 (2002) 2793-2796
31. Barrero A.F., Oltra J.E., Cuerva J.M., and Rosales A. J. Org. Chem. 67 (2002) 2566-2571
32. Cuerva J.M., Campaña A.G., Justicia J., Rosales A., Oller-López J.L., Robles R., Cárdenas D., Buñuel E., and Oltra J.E. Angew. Chem., Int. Ed. 45 (2006) 5522-5526
33. Schreiber S.L. Science 287 (2000) 1964-1969
34. For an overview on the biosynthesis and chemistry of terpenes, see:. Mann J., Davidson R.S., Hobbs J.B., Banthorpe D.V., and Harborne J.B. Natural Products: Their Chemistry and Biological Significance (1994), Longman Scientific & Technical, Essex pp 289-359
35. Barrero A.F., Oltra J.E., Morales V., and Álvarez M. J. Nat. Prod. 60 (1997) 1034-1035
36. Barrero A.F., Oltra J.E., and Álvarez M. Tetrahedron Lett. 39 (1998) 1401-1404
37. Rosales A., Estévez R.E., Cuerva J.M., and Oltra J.E. Angew. Chem., Int. Ed. 44 (2005) 319-322
38. Bermejo-Barrera J., Bretón J.L., Fajardo M., and González A.G. Tetrahedron Lett. (1967) 3475-3476
39. Bohlman F., and Zdero C. Phytochemistry 21 (1982) 647-651
40. Yamakawa K., Nishitani K., and Tominaga T. Tetrahedron Lett. (1975) 2829-2832
41. Grieco P.A., and Nishizawa M. J. Chem. Soc., Chem. Commun. (1976) 582-583
42. Ando M., Wada T., Kusaka H., Takase K., Hirata N., and Yanagi Y. J. Org. Chem. 52 (1987) 4792-4796
43. Higuchi Y., Shimoma F., Koyanagi R., Suda K., Mitsui T., Kataoka T., Nagai K., and Ando M. J. Nat. Prod. 66 (2003) 588-594
44. Barrero A.F., Oltra J.E., Álvarez M., and Rosales A. J. Org. Chem. 67 (2002) 5461-5469
45. Grieco P.A., and Nishizawa M. J. Org. Chem. 42 (1977) 1717-1720
46. Ogura M., Cordell G.A., and Farnsworth N.R. Phytochemistry 17 (1978) 957-961
47. Merkhatuly N., Zhokizhanova S.K., Balmagambetova L.T., and Adekenov S.M. Russ. J. Gen. Chem. 76 (2006) 1345-1346
48. Georgopapadakou N., and Walsh T.J. Science 264 (1994) 371-373
49. Odds F.C., Brown J.P., and Gow N.A.R. Trends Microbiol. 11 (2003) 272-279
50. Abad M.J., Ansuategui M., and Bermejo P. ARKIVOC (2007) 116-145
51. Barrero A.F., Oltra J.E., Álvarez M., Raslan D.S., Saúde D.A., and Akssira M. Fitoterapia 71 (2000) 60-64
52. Barrero A.F., Oltra J.E., and Poyatos J.A. Phytochemistry 42 (1996) 1427-1433
53. Barrero A.F., Oltra J.E., Poyatos J.A., Jiménez D., and Oliver E. J. Nat. Prod. 61 (1998) 1491-1496
54. Weinkove D., Poyatos J.A., Greiner H., Oltra J.E., Avalos J., Fukshansky L., Barrero A.F., and Cerdá-Olmedo E. Fungal Genet. Biol. 25 (1998) 196-203
55. Barrero A.F., Oltra J.E., Robinson J., Burke P.V., Jiménez D., and Oliver E. Steroids 67 (2002) 403-409
56. Cerdá-Olmedo E. In: Cerdá-Olmedo E., and Lipson E.D. (Eds). Phycomyces (1987), Cold Spring Harbor Laboratory, Plainview, NY 337-340