Enantioselective synthesis of (R)- and (S)-curcumene and curcuphenol: an efficient chemoenzymatic route

Tetrahedron Asymmetry

Volumn 18, Issue 21, 2007, Pages 2547-2553

  Kamal, Ahmed ^a   Malik, M Shaheer ^a   Shaik, Ahmad Ali ^a   Azeeza, Shaik ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE DERIVATIVE; BUTYRIC ACID; CURCUMENE; CURCUPHENOL; SESQUITERPENOID; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CATALYSIS; CHEMICAL REACTION; CURCUMA AROMATICA SALISB; CURCUMA LONGA; DRUG ACTIVITY; DRUG STRUCTURE; ENANTIOSELECTIVITY; ENZYME MECHANISM; HYDROLYSIS; KINETICS; PRIORITY JOURNAL; RHIZOME; SUBSTITUTION REACTION; SYNTHESIS;

EID: 36148934066     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.10.019     Document Type: Article

References (36)

1. Heathcock C.H. In: ApSimon J.W. (Ed). The Total Synthesis of Natural Products Vol. 2 (1973), Wiley, New York 197
2. Heathcock C.H., Graham S.L., Pirrung M.C., Plavac F., and White C.T. In: ApSimon J.W. (Ed). The Total Synthesis of Natural Products Vol. 5 (1981), Wiley and Sons, New York 35
3. Pirrung M.C., and Morehead A.T. In: Goldsmith D. (Ed). The Total Synthesis of Natural Products Vol. 10 (1997), Wiley and Sons, New York 29
4. Simonsen S.J. The Terpenes Vol. III (1952), Cambridge University Press p 18, 202
5. Honwad V.K., and Rao A.S. Tetrahedron 21 (1965) 2593
6. McEnroe F., and Fenical W. Tetrahedron 34 (1978) 1661
7. Butler M.S., Capon R.J., Nadeson R., and Beveridge A.A. J. Nat. Prod. 54 (1991) 619
8. El Sayed K.A., Yousaf M., Hamann M.T., Avery M.A., Kelly M., and Wipf P. J. Nat. Prod. 65 (2002) 1547
9. Wright A.E., Pomponi S.A., McConnell O.J., Kohmoto S., and McCarthy P.J. J. Nat. Prod. 50 (1987) 976
10. Fusetani N., Sugano M., Matsunaga S., and Hashimoto K. Experientia 43 (1987) 1234
11. Rodríguez A.D., and Vera B. J. Org. Chem. 66 (2001) 6364
12. Peng J., Franzblau S.G., Zhang F., and Hamann M.T. Tetrahedron Lett. 43 (2002) 9699
13. Armas H.T.D., Mootoo B.S., and Reynolds W.F. J. Nat. Prod. 63 (2000) 1593
14. Freyer A.J., Patil A.D., Killmer L., Zuber G., Myers C., and Johnson R.K. J. Nat. Prod. 60 (1997) 309
15. McEnroe F., and Fenical W. Tetrahedron 34 (1978) 1661
16. Bohlman F., and Lonitz M. Chem. Ber. 111 (1978) 843
17. Cichewicz R.H., Clifford L.J., Lassen P.R., Cao X., Freedman T.B., Nafie L.A., Deschamps J.D., Kenyon V.A., Flanary J.R., Holman T.R., and Crews P. Bioorg. Med. Chem. Lett. 13 (2005) 5600
18. Meyers A.I., and Stoianova D. J. Org. Chem. 62 (1997) 5219
19. Hagiwara H., Okabe T., Ono H., Kamat V.P., Hoshi T., Suzuki T., and Ando M. J. Chem. Soc., Perkin Trans. 1 (2002) 895
20. Harmata M., Hong X., and Barnes C.L. Tetrahedron Lett. 44 (2003) 7261
21. Schmalz H.G., de Koning C.B., Bernicke D., Siegel S., and Pfletschinger A. Angew. Chem., Int. Ed. 38 (1999) 1620
22. Takano S., Yanase M., Sugihara T., and Ogasawara K. J. Chem. Soc., Chem. Commun. (1988) 1538
23. Tamao K., Hayashi T., Matsumoto H., Yamamato H., and Kumada M. Tetrahedron Lett. 20 (1979) 2155
24. Sugahara T., and Ogasawara K. Tetrahedron: Asymmetry 9 (1998) 2215
25. Lu J., Xie X., Chen B., She X., and Pan X. Tetrahedron: Asymmetry 16 (2005) 1435
26. Fuganti C., and Serra S. J. Chem. Soc., Perkin Trans. 1 (2000) 3758
27. Fuganti C., Serra S., and Dulio A. J. Chem. Soc., Perkin Trans. 1 (1999) 279
28. Fuganti C., and Serra S. Synlett (1998) 1252
29. Ono M., Ogura Y., Hatogai K., and Akita H. Tetrahedron: Asymmetry 6 (1995) 1829
30. Ono M., Yamamoto Y., and Akita H. Chem. Pharm. Bull. 43 (1995) 553
31. Kamal A., Krishnaji T., and Khan M.N.A. J. Mol. Catal. B 47 (2007) 1
32. Kamal A., Shaik A.A., Azeeza S., Malik M.S., and Sandbhor M. Tetrahedron: Asymmetry 17 (2006) 2890
33. Kamal A., Shaik A.A., Sandbhor M., Malik M.S., and Azeeza S. Tetrahedron: Asymmetry 17 (2006) 2876
34. Kamal A., Ramana K.V., and Rao M.V. J. Org. Chem. 66 (2001) 997
35. Varadharaj G., Hazell K., and Reeve C.D. Tetrahedron: Asymmetry 9 (1998) 1191
36. Makita N., Hoshino Y., and Yamamoto H. Angew. Chem., Int. Ed. 42 (2003) 941