Lipase-catalysed resolution of cis-1-ethoxycarbonyl-2-hydroxy-cyclohexane: Enantioselective total synthesis of 10-ethyl-trinem

Tetrahedron Asymmetry

Volumn 8, Issue 1, 1997, Pages 15-17

  Panunzio, Mauro ^a   Camerini, Roberto ^a   Mazzoni, Andrea ^a   Donati, Daniele ^b   Marchioro, Carla ^b   Pachera, Roberta ^b  

^a CNR   (Italy)

^b GSK   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

10 ETHYLTRINEM; PENEM DERIVATIVE; TRIACYLGLYCEROL LIPASE; TRINEM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0031026885     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00489-2     Document Type: Article

References (10)

1. Jackson, M. P.; Roberts, S. M.; Davalli, S.; Donati, D.; Marchioro, C.; Perboni, A.; Proviera, S.; Rossi, T. J. Chem. Soc. Perkin Trans. 1 1996, 2029 and Ref. therein cited.
2. Camerini, R.; Panunzio, M.; Bonanomi, G.; Donati, D.; Perboni, A. Tetrahedron Lett. 1996, 37, 2467.
3. Cainelli, G.; Panunzio, M.; Giacomini, D.; Bandini, E.; Martelli, G.; Spunta, G. In Chemical Synthesis Gnosis to Prognosis; C. Chatgilialoglu and V. Snieckus, Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1996; Vol. Serie E: Applied Sciences Vol. 320; pp. 25-60 and Ref. therein cited.
4. See e.g.: Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071.
5. Resolution of racemic acetate in one step is currently under investigation.
6. Spiliotis, V.; Papahatjia, D.; Ragoussis, N. Tetrahedron Lett. 1990, 31, 1615.
7. Panunzio, M.; Camerini, R.; Pachera, R.; Donati, D.; Marchioro, C.; Perboni, A. Tetrahedron: Asymm. 1996, 7, 2969.
8. 3): 6.01-5.91 (1H, m); 5.45-5.38 (1H, m); 5.26-5.22 (1H, m); 4.82-4.76 (1H, m); 4.69-4.63 (1H, m); 3.90-3.85 (1H, J=3.06, 10.14); 3.46-3.42 (1H, m); 3.16-3.10 (1H, m); 2.80-2.78 (1H, m); 1.06-0.96 (3H, t).
9. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
10. The epimerization of the C-8 stereogenic center is quite unusual and the intimate mechanism is, at present, obscure. Work is in progress to clarify this aspect.