First enantioselective synthesis and absolute stereochemistry assignment of new monoterpene aldehyde-esters from Bupleurum gibraltaricum

European Journal of Organic Chemistry

Volumn , Issue 17, 2007, Pages 2802-2807

  Brémond, Paul ^a   Audran, Gérard ^a   Juspin, Thierry ^a   Monti, Honoré ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Absolute configuration determination; Enantioselective synthesis; Natural products; Terpene

Indexed keywords

EID: 34250799716     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601080     Document Type: Article

References (24)

1. F. Bohlmann, C. Zdero, M. Grenz, Chem. Ber. 1975, 108, 2822-2823.
2. A. F. Barrero, A. Haïdour, F. Reyes, J. Nat. Prod. 1998, 61, 506-507.
3. Isoferulyl angelate [(-)-1] has also been extracted from seeds of Eryngium paniculatum Cav. and Comby ex. Delar L., and was found to inhibit germination of velvetleaf (Abutilon theophrasti Medic.) G. F. Spencer, J. Nat. Prod. 1986, 49, 924-926.
4. A. M. Cauwet-Marc, J. Carbonnier, J. Agric. Bot. Appl. 1978, 25, 51-59.
5. a) J. Cabo, M. M. Cabo, J. Jimenez, C. Navarro, M. A. Ocete, Plantes Med. Phytother. 1986, 20, 178-182;
6. b) J. Cabo, J. Jimenez, M. A. Ocete, A. Zarzuelo, Fitoterapia 1987, 58, 33-38;
7. c) M. A. Ocete, S. Risco, A. Zarzuelo, J. Jimenez, J. Ethnopharmacol. 1989, 25, 305-313.
8. A. Velasco-Negueruela, M. J. Perez-Alonso, J. Pala-Paul, A. Camacho, A. M. Fernandez Ocana, C. Fernandez Lopez, J. Altarejos, M. C. Garcia Vallejo, J. Essent. Oil Res. 1998, 10, 9-19.
9. a) By use of the standard chemical software, the absolute configuration of C-1 in (+)-3 is determined as S.
10. This assignment is incorrect; b) J.-M. Galano, G. Audran, H. Monti, Tetrahedron 2000, 56, 7477-7481.
11. J.-P. Uttaro, G. Audran, E. Palombo, H. Monti, J. Org. Chem. 2003, 68, 5407-5410.
12. E. J. Corey, A. Venkateswarlu, J. Am. Chem. Soc. 1972, 94, 6190-6191.
13. Y. Tanada, K. Mori, Eur. J. Org. Chem. 2003, 848-854.
14. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3th ed., John Wiley & Sons, 1999, p. 127-141.
15. a) K. C. Nicolaou, S. P. Seitz, M. R. Pavia, N. A. Petasis, J. Org. Chem. 1979, 44, 4011-4013;
16. b) For the preparation of HF·pyridine buffered with excess pyridine in THF see: B. M. Trost, C. G. Caldwell, E. Murayama, D. Heissler, J. Org. Chem. 1983, 48, 3252-3265.
17. a) W. M. Hoskins, D. H. G. Crout, J. Chem. Soc., Perkin Trans. 1 1977, 538-544;
18. b) P. J. Beeby, Tetrahedron Lett. 1977, 18, 3379-3382;
19. c) J. Inakaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn 1979, 52, 1989-1993;
20. d) J. Nakayama, Y. Nakamura, T. Tajiri, M. Hoshino, Heterocycles 1986, 24, 637-640;
21. e) S. Bal-Tembe, D. N. Bhedi, N. J. de Souza, R. H. Rupp, Heterocycles 1987, 26, 1239-1249;
22. f) B. Hartmann, A. M. Kanazawa, J.-P. Deprés, A. E. Greene, Tetrahedron Lett. 1991, 32, 5077-5080.
23. A. C. Savoca, in Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, vol. 2, p. 1497-1503.
24. H. E. Gottlieb, V. Kotlyar, A. Nudelman, J. Org. Chem. 1997, 62, 7512-7515.