Lipase-promoted access to phenolic herbertane-type sesquiterpenes: (+)-1,14-Herbertenediol, (-)-α-herbertenol, (-)-herbertenediol and their enantiomers

European Journal of Organic Chemistry

Volumn , Issue 24, 2004, Pages 5092-5099

  Acherar, Samir ^a   Audran, Gérard ^a   Fotiadu, Frédéric ^a   Monti, Honoré ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Asymmetric synthesis; Conformational analysis; Lipases; Natural products

Indexed keywords

1,14 HERBERTENEDIOL; ALPHA HERBERTENOL; BENZENE; CUPARENE; HERBERTENEDIOL; PHENOL DERIVATIVE; SESQUITERPENE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; MOLECULAR MECHANICS; STEREOCHEMISTRY;

EID: 11144290659     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400395     Document Type: Article

References (40)

1. H. Irita, T. Hashimoto, Y. Fukuyama, Y. Asakawa, Phytochemistry 2000, 55, 247-253.
2. A. Matsuo, S. Yuki, M. Nakayama, J. Chem. Soc., Perkin Trans, 1 1986, 701-710.
3. Racemic synthesis of phenolic herbertanes: [3a] T. Eicher, F. Servet, A. Speicher, Synthesis 1996, 863-870.
4. [3b] Y. Fukuyama, Y. Kiriyama, M. Kodama, Tetrahedron Lett. 1996, 37, 1261-1264.
5. [3c] D. C. Harrowven, J. C. Hannam, Tetrahedron 1999, 55, 9333-9340.
6. [3d] A. Pal, P. D. Gupta, A. Roy, D. Mukherjee, Tetrahedron Lett. 1999, 40, 4733-4734.
7. [3e] P. D. Gupta, A. Pal, A. Roy, D. Mukherjee, Tetrahedron Lett. 2000, 41, 7563-7566.
8. [3f] Y. Fukuyama, H. Yuasa, Y. Tonoi, K. Harada, M. Wada, Y. Asakawa, T. Hashimoto, Tetrahedron 2001, 57, 9299-9307.
9. [3g] A. Srikrishna, M. S. Rao, Tetrahedron Lett. 2001, 42, 5781-5782.
10. [3h] A. Abad, C. Agullò, A. C. Cuñat, D. Jimenez, R. H. Perni, Tetrahedron 2001, 57, 9727-9735.
11. [3i] A. Srikrishna, M. S. Rao, Tetrahedron Lett. 2002, 43, 151-154.
12. [3j] A. Srikrishna, M. S. Rao, Synlett 2002, 340-342.
13. [3k] A. Srikrishna, G. Satyanarayana, Tetrahedron Lett. 2003, 44, 1027-1030.
14. [3l] S. P. Chavan, R. K. Kharul, R. R. Kale, D. A. Khobragade, Tetrahedron 2003, 59, 2737-2741.
15. [3m] T. Paul, A. Pal, P. D. Gupta, D. Mukherjee, Tetrahedron Lett. 2003, 44, 737-740.
16. [3n] A. Srikrishna, M. S. Rao, Eur. J. Org. Chem. 2004, 499-503.
17. Enantioselective synthesis of phenolic herbertanes: [4a] G. Bringmann, T. Pabst, D. S. Rycroft, J. D. Connolly, Tetrahedron Lett. 1999, 40, 483-486.
18. [4b] A. Abad, C. Agullò, A. C. Cuñat, R. H. Perni, J. Org. Chem. 1999, 64, 1741-1744.
19. [4c] A. P. Degnan, A. I. Meyers, J. Am. Chem. Soc. 1999, 121, 2762-2769.
20. [4d] G. Bringmann, T. Pabst, P. Henschel, J. Kraus, K. Peters, E. M. Peters, D. S. Rycroft, J. D. Connolly, J. Am. Chem. Soc. 2000, 122, 9127-9133.
21. [4e] A. Abad, C. Agullò, A. C. Cuñat, R. H. Perni, Tetrahedron: Asymmetry 2000, 11, 1607-1615.
22. [4f] G. Bringmann, J. Hinrichs, T. Pabst, P. Henschel, K. Peters, E. M. Peters, Synthesis 2001, 155-167.
23. [4g] Y. Fukuyama, K. Matsumoto, Y. Tonoi, R. Yokoyama, H. Takahashi, H. Minami, H. Okazaki, Y. Mitsumoto, Tetrahedron 2001, 57, 7127-7135.
24. [4h] G. Bringmann, T. Pabst, P. Henschel, M. Michel, Tetrahedron 2001, 57, 1269-1275.
25. [4i] Y. Kita, J. Futamura, Y. Ohba, Y. Sawama, J. K. Ganesh, H. Fujioka, J. Org. Chem. 2003, 68, 5917-5924.
26. [4j] Y. Kita, J. Futamura, Y. Ohba, Y. Sawama, J. K. Ganesh, H. Fujioka, Tetrahedron Lett. 2003, 44, 411-413.
27. [4k] A. Srikrishna, N. C. Babu, M. S. Rao, Tetrahedron 2004, 60, 2125-2130.
28. S. Acherar, G. Audran, N. Vanthuyne, H. Monti, Tetrahedron: Asymmetry 2003, 14, 2413-2418.
29. S. Acherar, G. Audran, F. Cecchin, H. Monti, Tetrahedron 2004, 60, 5907-5912.
30. L. J. Dolby, C. A. Elliger, S. Esfandiari, K. S. Marshall, J. Org. Chem. 1968, 33, 4508-4511.
31. [8a] A. E. Greene, J.-P. Lansard, J.-L. Luche, C. Petrier, J. Org. Chem. 1984, 49, 931-932.
32. [8b] C. Petrier, J. C. de Souza Barbosa, C. Dupuy, J.-L. Luche, J. Org. Chem. 1985, 50, 5761-5765.
33. A. L. Gemal, J.-L. Luche, J. Am. Chem. Soc. 1981, 103, 5454-5459.
34. D. F. Taber, M. J. Hennessy, J. P. Louey, J. Org. Chem. 1992, 57, 436-441.
35. [11a] J. R. Mapple, U. Dinur, A. T. Hagler, Proc. Natl. Acad. Sci. USA 1988, 85, 5350-5354.
36. [11b] J. R. Mapple, M.-J. Hwang, T. P. Stockfish, U. Dinur, M. Waldman, C. S. Ewig, A. T. Hagler, J. Comput. Chem. 1994, 15, 162-182.
37. [11c] M.-J. Hwang, T. P. Stockfish, A. T. Hagler, J. Am. Chem. Soc. 1994, 116, 2515-2525.
38. The CFF91 force field, as implemented in the Cerius2 4.0 software package from Accelrys Inc., was used throughout this study (modules Open Force Field and Conformer).
39. D. H. R. Barton, S. W. McCombie, J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585.
40. Similar stereoselective alkylations have been conducted on a cyclopentene framework or using a one-pot intramolecular cyclisation/alkylation sequence. See refs.[3i,3m]