Use of lipase-catalyzed kinetic resolution for the enantioselective approach toward sesquiterpenes containing quaternary centers: the cuparane family

Author:

Acherar Samir,Audran Gérard,Vanthuyne Nicolas,Monti Honoré

Publisher

Elsevier BV

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis

Reference15 articles.

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2. Recent syntheses of racemic cuparene: (a) Kametani, T.; Tsubuki, M.; Nemoto, H. J. Chem. Soc., Perkin Trans. 1 1980, 759–761; (b) Reetz, M. T.; Westermann, J.; Steinbach, R. J. Chem. Soc., Chem. Commun. 1981, 237–239; (c) Kametani, T.; Kawamura, K.; Tsubuki, M.; Honda, T. J. Chem. Soc., Chem. Commun. 1985, 1324–1325; (d) Shiao, M.-J.; Liang, D.; Ku, C.-S.; Yang, C.-H. Synth. Commun. 1988, 18, 1553–1563; (e) Bovicelli, P.; Mincione, E. Synth. Commun. 1988, 18, 2037–2050; (f) Ishibashi, H.; So, T. S.; Nakatani, H.; Minami, K.; Ikeda, M. J. Chem. Soc., Chem. Commun. 1988, 827–828; (g) Bailey, W. F.; Khanolkar, A. D. Tetrahedron 1991, 47, 7727–7738; (h) Mandelt, K.; Fitjer, L. Synthesis 1998, 1523–1526; (i) Ho, T.-L.; Chang, M.-H. J. Chem. Soc., Perkin Trans. 1 1999, 2479–2482.

3. Syntheses of enantiomerically enriched cuparene: (a) Subba Rao, H. N.; Damodaran, N. P.; Dev, S. Tetrahedron Lett. 1968, 2213–2214; (b) Abad, A.; Agulló, C.; Arnó, M.; Cuñat, A. C.; Garcia, M. T.; Zaragozá, R. J. J. Org. Chem. 1996, 61, 5916–5919; (c) Fuganti, C.; Serra, S. J. Org. Chem. 1999, 64, 8728–8730.

4. Syntheses of racemic tochuinyl acetate: (a) Nakatani, H.; So, T. S.; Ishibashi, H.; Ikeda, M. Chem. Pharm. Bull. 1990, 38, 1233–1237; (b) Taber, D. F.; Hennessy, M. J.; Louey, J. P. J. Org. Chem. 1992, 57, 436–441; (c) Srikrishna, A.; Reddy, T. J.; Kumar, P. P.; Vijaykumar, D. Synlett 1996, 67–68; (d) Srikrishna, A.; Reddy, T. J. Tetrahedron 1998, 54, 8133–8140; (e) Srikrishna, A.; Rao, M. S. Tetrahedron Lett. 2002,43, 151–154; (f) Paul, T.; Pal, A.; Gupta, P. D.; Mukherjee, D. Tetrahedron Lett. 2003, 44, 737–740.

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