First enantiospecific synthesis of (-)-parvifoline and (-)-curcuquinone

Journal of Organic Chemistry

Volumn 71, Issue 23, 2006, Pages 8986-8988

  Chavan, Subhash P ^a   Thakkar, Mahesh ^a   Jogdand, Ganesh F ^a   Kalkote, Uttam R ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; KETONES; SYNTHESIS (CHEMICAL);

CITRONELLAL; CURCUQUINONE; ENANTIOSPECIFIC SYNTHESIS; PARVIFOLINE;

AROMATIC COMPOUNDS;

CITRONELLAL; CURCUQUINONE; NATURAL PRODUCT; PARVIFOLINE; PHENOL DERIVATIVE; SESQUITERPENOID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; ENANTIOMER; RING CLOSING METATHESIS; SYNTHESIS;

MOLECULAR STRUCTURE; SESQUITERPENES; STEREOISOMERISM;

EID: 33750848809     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061730d     Document Type: Article

References (28)

1. Bohlmann, F.; Zdero, C. Chem. Ber. 1977, 110, 468-473.
2. (a) Joseph-Nathan, P.; Hernandez, J. D.; Roman, L. U.; Garcia, G. E.; Mendoza, V.; Mendoza, S. Photochemistry 1982, 21, 1129-1132.
3. (b) Joseph-Nathan, P.; Hernandez, J. D.; Roman, L. U.; Garcia, G. E.; Mendoza, V. Phytochemistry 1982, 21, 669-672.
4. (c) Garcia, G. E.; Mendoza, V.; Guzman B., J. A. J. Nat. Prod. 1988, 51, 150-151.
5. (a) Joseph-Nathan, P.; Hernandez-Medel, M.; Martinez, E.; Rojas-Gardida, M.; Cerda, C. M. J. Nat. Prod. 1988, 51, 675-689.
6. (b) Garcia, G. E.; Mendoza, V.; Guzman, B. A. J. Nat. Prod. 1987, 50, 1055-1058.
7. McEnroe, F. J.; Fenical, W. Tetrahedron 1978, 34, 1661-1664.
8. Takabatake, K.; Nishi, I.; Shindo, M.; Shishido, K. J. Chem. Soc., Perkin Trans. 1 2000, 1807-1808.
9. Chavan, S. P.; Dhondge, V. D.; Patil, S. S.; Rao, T. S.; Govande, C. A. Tetrahedron: Asymmetry 1997, 8, 2517-2518.
10. Chavan, S. P.; Thakkar, M.; Kharul, R. K.; Pathak, A. B.; Bhosekar, A. V.; Bhadbhade, M. V. Tetrahedron 2005, 61, 3873-3879.
11. (a) Villagomez-Ibarra, R.; Joseph-Nathan, P. Tetrahedron Lett. 1994, 35, 4771-4772.
12. (b) Grimm, E. L.; Levac, S.; Coutu, M. L. Tetrahedron Lett. 1994, 35, 5369-5372.
13. (c) Villagomez-Ibarra, R.; Alvarez-Cisneros, C.; Joseph-Nathan, P. Tetrahedron 1995, 51, 9285-9300.
14. (d) Covarrubias-Zuniga, A.; Cantu, P.; Maldonado, L. A. J. Org. Chem. 1998, 63, 2918-2921.
15. (e) Bhowmik, D. R.; Venkateswaran, R. V. Tetrahedron Lett. 1999, 40, 7431-7433.
16. (a) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832.
17. (b) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758-3764.
18. (c) Takabatake, K.; Nishi, I.; Shindo, M.; Shishido, K. J. Chem. Soc., Perkin Trans. 1 2000, 1807-1808.
19. (d) Yoshimura, T.; Kisyuka, H.; Kamei, T.; Takabatake, K.; Shindo, M.; Shishido, K. Arkivoc 2003, 247-255.
20. (e) Minatti, A.; Heinz Dotz, K. J. Org. Chem. 2005, 70, 3745-3748.
21. (a) Ghisalberti, E. L.; Jeferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627-1630.
22. (b) Hagiwara, H.; Tomoyuki, O.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 895-900.
23. Rubottom, G. M.; Gruber, J. M. J. Org. Chem. 1978, 43, 1599-1602.
24. Dauben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682-685.
25. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
26. (a) Michalak, M.; Wicha, J. Synlett 2005, 50, 2277-2280.
27. (b) Boyer, F. D.; Hanna, I. Eur. J. Org. Chem. 2006, 471-482.
28. (c) Hoffmann, T.; Gmeiner, P. Synlett 2002, 6, 1014-1016.