Lipase catalysed kinetic resolution of 2-Nitroalcohol: Total synthesis of taxol side chain and (-)-bestatin

Letters in Organic Chemistry

Volumn 4, Issue 4, 2007, Pages 234-235

  Gogoi, Naminita ^a   Borah, Jagat C ^a   Boruwa, Joshodeep ^a   Barua, Nabin ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

( ) bestatin; Lipase catalysed kinetic resolution; Taxol side chain

Indexed keywords

EID: 35649020240     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017807781024192     Document Type: Article

References (26)

1. (a) Umezawa, K.; Ikeda, Y.; Uchihata, Y.; Naganawa, H.; Kondo, S. J. Org. Chem., 2000, 65, 459;
2. (b) Babine, R. L.; Bender, S. E. Chem. Rev., 1997, 97, 1359.
3. (a) Cole, D.C. Tetrahedron, 1994, 50, 9517;
4. (b) Cardillo, G.; Tomasini, C. Chem. Soc. Rev., 1996, 29, 117.
5. (a) Denis, J.-N.; Correa, A.; Greene, A.E. J. Org. Chem., 1990, 55, 1957;
6. (b) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron, 2001, 57, 2139
7. (c) Chaudary, B.M.; Chowdari, S.N.; Madhi, S.; Kantam, M.L. J. Org. Chem., 2003, 68, 1736.
8. Sugimura, H.; Miura, M.; Yamada, N. Tetrahedron Asymmetry, 1997, 8, 4089.
9. (a) Pearson, W.H.; Hines, J.H. J. Org. Chem., 1989, 54, 4235;
10. (b) Nemato, H.; Ma, R.; Suzuki, I.; Shibuya, M. Org. Lett., 2000, 2, 4245;
11. (c) Righi, G.; D'Achille, D.; Pescatore, G.; Bonini, C.J. Tetrahedron Lett., 2003, 44, 6999.
12. Borah, J. C.; Boruwa, J.; Kalita, B.; Hazarika, A.; Barua, N. C. Indian J. Chem., 2005, 44B, 331.
13. Guieysse, D.; Salagnad, C.; Monsau, P.; Simeon, M.; Tran, Y. Tetrahedron Assymmetry, 2003, 14, 1807.
14. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc., 1971, 93, 2325.
15. For a review on synthesis of taxol side chain see: Borah, J. C.; Boruwa, J.; Barua, N. C. Curr. Org. Synth., 2007, 4, 175.
16. The quantity of lipase was not optimized. The lipase collected after the reaction was washed with ether, dried in air for 5 min and stored below 5°C. The lipase retains full activity and can be reused at least three times.
17. The enantiomeric purity of the nitroalcohols 4(b) and 11 were determined in Chiracel OD-H column (hexane-2-propanol, 230 nm & 254 nm). Enantiomeric purity of the Acetates 4(a) and 10 were also determined by Chiracel OD-H column (hexane-2-propanol, 230 nm & 254 nm).
18. Borah, J.C.; Gogoi, S.; Boruwa, J.; Kalita, B.; Barua, N.C. Tetrahedron Lett., 2004, 45, 3689.
19. Wang, Z.-M.; Kolb, H. C.; Sharpless, K. B. J. Org. Chem., 1994, 59, 5104.
20. (a) Umezawa, H.; Aoyagi, T.; Suda, H.; Hamada, M.; Takeuchi, T. J. Antibiot., 1976, 29, 97;
21. (b) Nishino, N.; Powers, J. C. Biochemistry, 1979, 18, 4340.
22. Nakamura, H.; Suda, H.; Takita, T.; Aoyagi, T.; Umezawa, H.; Iitaka, Y. J. Antibiot., 1976, 29, 102.
23. Ino, K.; Goto, S.; Nomura, S.; Isobe, K,-I.; Nawa, A.; Okamoto, T.; Tomoda, Y. Anticancer Res., 1995, 15, 2081.
24. Dzoljicacute, E.; Varagicacute, V. M. In Fundamental Clin. Pharmacol., 1987, 1, 307.
25. Gogoi, N.; Boruwa, J.; Barua, N. C. Tetrahedron Lett., 2005, 46, 7581.
26. 2.