Ti(III)-promoted cyclizations. Application to the synthesis of (E)-endo-bergamoten-12-oic acids. Moth oviposition stimulants isolated from Lycopersicon hirsutum

Tetrahedron

Volumn 62, Issue 38, 2006, Pages 8933-8942

  Bermejo, Francisco A ^a   Fernández Mateos, Alfonso ^a   Marcos Escribano, Andrés ^a   Martín Lago, Rodrigo ^a   Mateos Burón, Lydia ^a   Rodríguez López, María ^a   Rubio González, Rosa ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Halomethacrylates; (E) endo Bergamoten 12 oic acids; (S) (+) Carvone; Sesquiterpenoids

Indexed keywords

8,9 EPOXYCARVONE; ACID; ALKENE; BETA BERGAMOTEN 12 OIC ACID; BETA IODOMETHACRYLATE; CARVONE; METHACRYLIC ACID DERIVATIVE; TITANIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DEPROTECTION REACTION; EGG LAYING; LYCOPERSICON HIRSUTUM; MOTH; PRIORITY JOURNAL; SYNTHESIS; TOMATO;

LEPIDOPTERA; LYCOPERSICON HIRSUTUM;

EID: 33746805390     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.07.020     Document Type: Article

References (45)

1. Coates R.M., Denissen J.F., Juvik J.A., and Babka B.A. J. Org. Chem. 53 (1988) 2186-2192
2. Mori K., and Matsushima Y. Synthesis (1994) 417-421
3. Wilcox J., Howland A.F., and Campbell R.E. Tech. Bull.-U.S. Dep. Agric. (1956) 1147
4. Gibson T.W., and Erman W.F. J. Am. Chem. Soc. 91 (1969) 4771-4778
5. Hortmann A.G., and Youngstrom R.E. J. Org. Chem. 34 (1969) 3392-3395
6. Hobbs P.D., and Magnus P.D. J. Am. Chem. Soc. 98 (1976) 4594-4600
7. Rico R., and Bermejo F. Tetrahedron Lett. 36 (1995) 7889-7892
8. Bermejo F., Rico-Ferreira R., Bamidele-Sanni S., and Garcia-Granda S. J. Org. Chem. 66 (2001) 8287-8292
9. Rico R., Zapico J., Bermejo F., Bamidele Sanni S., and García Granda S. Tetrahedron: Asymmetry 9 (1998) 293-303
10. For pioneering work on Ti(III)-promoted transformations, see:
11. Nugent W.A., and RajanBabu T.V. J. Am. Chem. Soc. 110 (1988) 8561-8562
12. RajanBabu T.V., and Nugent W.A. J. Am. Chem. Soc. 111 (1989) 4525-4527
13. RajanBabu T.V., Nugent W.A., and Beatti M.S. J. Am. Chem. Soc. 112 (1990) 6408-6409
14. RajanBabu T.V., and Nugent W.A. J. Am. Chem. Soc. 116 (1994) 986-997 For the catalytic version see:
15. Gansäuer A. Synlett (1998) 801-809
16. Gansäuer A., Bluhm H., and Pierobon M. J. Am. Chem. Soc. 120 (1998) 12849-12859
17. Gansäuer A., and Bauer D. Eur. J. Org. Chem. (1998) 2673-2676
18. Gansäuer A., Lauterbach T., Bluhm H., and Noltemeyer M. Angew. Chem., Int. Ed. 38 (1999) 2909-2910
19. Gansäuer A., and Pierobon M. Synlett (2000) 1357-1359
20. The synthesis of cyclic terpenoids based on the radical opening of acyclic epoxypolyenes has been reported widely:
21. Gansäuer A., Pierobon M., and Bluhm H. Synthesis (2001) 2500-2520
22. Nakai K., Kamoshita M., Doi T., Yamada H., and Takahashi T. Tetrahedron Lett. 42 (2001) 7855-7857
23. Haruo Y., Hasegawa T., Tanaka H., and Takahashi T. Synlett (2001) 1935-1937
24. Barrero A.F., Cuerva J.M., Herrador M.M., and Valdivia M.V. J. Org. Chem. 66 (2001) 4074-4078
25. Barrero A.F., Cuerva J.M., Alvarez-Manzaneda E.J., Oltra J.E., and Chahboun R. Tetrahedron Lett. 43 (2002) 2793-2796
26. Barrero A.F., Oltra J.E., Cuerva J.M., and Rosales A. J. Org. Chem. 67 (2002) 2566-2571
27. Gansäuer A., Lauterbach T., and Natayan S. Angew. Chem., Int. Ed. 42 (2003) 5556-5573
28. Justicia J., Oltra J.E., and Cuerva J.M. J. Org. Chem. 69 (2004) 5803-5806
29. Rosales A., Estévez R.E., Cuerva J.M., and Oltra J.E. Angew. Chem., Int. Ed. 44 (2005) 319-322
30. Rosales A., Estévez R.E., Cuerva J.M., and Oltra J.E. Angew. Chem., Int. Ed. 44 (2005) 323-326
31. Justicia J., Rosales A., Buñuel E., Oller-López J.L., Valdivia M., Haidour A., Oltra J.E., Barrero A.F., Cardenas D.J., and Cuerva J.M. Chem.-Eur. J. 10 (2004) 1778-1788
32. The preparation and structural assessment of (-)-8,9-epoxycarvone have been reported:. Nishimura H., Hiramoto S., Mizutani J., Noma Y., Furusaki A., and Matsumoto T. Agric. Biol. Chem. 47 (1983) 2697-2699
33. Weinges K., and Schwarz G. Liebigs Ann. Chem. (1993) 811-814
34. Beta hydrogen elimination with Ti(III) was reported for the first time by. Fernández-Mateos A., Martín de la Nava E., Pascual Coca G., Ramos Silvo A., and Rubio González R. Org. Lett. 1 (1999) 607-609
35. Fernández-Mateos A., Mateos Burón L., Martín de la Nava E., Rabanedo Clemente R., Rubio González R., and Sanz Gonzalez F. Synlett (2004) 2553-2557
36. For a similar rationalization of the stereochemical outcome of a Ti-promoted transformation, see:. Sandoval C., and Bermejo F. J. Org. Chem. 69 (2004) 5275-5280
37. Yasuda M., Onishi Y., Ueba M., Miyai T., and Baba A. J. Org. Chem. 66 (2001) 7741-7744
38. By reaction with mesyl chloride in pyridine the primary monoacetates of 9 and 10 led separately to (S)-(+)-carvone as a result of Grob fragmentation processes.
39. Oh H., Gloer J.B., and Shearer C.A. J. Nat. Prod. 62 (1999) 497-501
40. Transformation of 6 into 16 was successfully achieved by following the procedure described by Mori (see Ref. 2).
41. Dess D.B., and Martin J.C. J. Org. Chem. 48 (1983) 4155-4156
42. Miyaura N., Ishiyama T., Ishikawa M., and Suzuki A. Tetrahedron Lett. 27 (1986) 6369-6372
43. Chemler S.R., Trauner D., and Danishefsky S. Angew. Chem., Int. Ed. 40 (2001) 4544-4568
44. Baker R., and Castro J.L. J. Chem. Soc., Perkin Trans. 1 (1995) 5386-5387
45. Still W.C., Kahn M., and Mitra A.R. J. Org. Chem. 43 (1978) 2923-2925