Lipase-mediated resolution of cis-4-cumyloxy-2-cyclopenten-1-ol and its utilization for enantioconvergent preparation of (-)-oxabicyclo[3.3.0]oct-6- en-3-one

Synlett

Volumn , Issue 11, 1999, Pages 1754-1756

  Nakashima, Hiromi ^a   Sato, Masayuki ^a   Taniguchi, Takahiko ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Chiral building block; Enantioconvergent synthesis; Kinetic resolution; Lipase mediated kinetic transesterification; Prostaglandin building block

Indexed keywords

BICYCLO COMPOUND; CYCLOPENTADIENE DERIVATIVE; CYCLOPENTENE DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; ENANTIOMER; PROSTAGLANDIN SYNTHESIS; SYNTHESIS;

EID: 0032705783     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2956     Document Type: Article

References (16)

1. Corey, E. J.; Fuchs, P. L. J. Am. Chem. Soc. 1972, 94, 4014.
2. Partridge, J. J.; Chadha, N. K.; Uskokovic, M. R. J. Am. Chem. Soc. 1973, 95, 7171.
3. Myers, A. G.; Liang, J.; Hammond, M. Tetrahedron Lett. 1999, 40, 5129.
4. Takano, S.; Tanigawa, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1976, 189.
5. A pertinent review, see: Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769.
6. Sugahara, T.; Kuroyanagi, Y.; Ogasawara, K. Synthesis 1996, 1101.
7. Takano, S.; Kasahara, C.; Ogasawara, K. Heterocycles 1981, 16, 605.
8. Takano, S.; Iwabuchi, Y.; Takahashi, M.; Ogasawara, K. Chem. Pharm. Bull. 1986, 34, 3445.
9. Haubenstock, H.; Mennit, P. G.; Bulter, P. E. J. Org. Chem. 1970, 35, 3208: Stork, G.: Isobe, M. J. Am. Chem. Soc., 1975, 97, 6260.
10. Haubenstock, H.; Mennit, P. G.; Bulter, P. E. J. Org. Chem. 1970, 35, 3208: Stork, G.: Isobe, M. J. Am. Chem. Soc., 1975, 97, 6260.
11. Gemal, A. L.; Luche, T. L. J. Am. Chem. Soc., 1981, 103, 5454.
12. 2O, then EtOAchexane 1:1) to give (-)-7 (2.44 g, 84%).
13. Sugahara, T.; Ogasawara, K. Synlett 1996, 319.
14. Wick, A. E.; Felix, D.; Steen, K.; Eschenmoser, A. Helv. Chim. Acta 1964, 47, 2425.
15. Johnson, W, S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T. J.; Lee, T.-t.; Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1970, 92, 741.
16. Myers, A. G.; Hammond, M.; Wu, Y. Tetrahedron Lett. 1996, 37, 3083.