Lipase-catalyzed kinetic resolution of 3-chloro-2-hydroxyalkanoates. Its application for the synthesis of (-)-disparlure

Tetrahedron Asymmetry

Volumn 8, Issue 3, 1997, Pages 375-379

  Tsuboi, Sadao ^a   Yamafuji, Nobuyuki ^a   Utaka, Masanori ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DISPARLURE; PHEROMONE; TRIACYLGLYCEROL LIPASE;

ARTICLE; DRUG SYNTHESIS; ESTERIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION;

EID: 0031051723     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00529-0     Document Type: Article

References (23)

1. Tsuboi, S.; Furutani, H.; Ansari, M. H.; Sakai, T.; Utaka, M.; Takeda, A. J. Org. Chem. 1993, 58, 486.
2. (a) Mori, K.; Takigawa, T.; Matsui, M. Tetrahedron Lett. 1976, 44, 3953.
3. (b) Mori, K.; Takigawa, T.; Matsui, M. Tetrahedron. 1979, 35, 833.
4. (c) Mori, K.; Ebata, T. Tetrahedron Lett. 1981, 22, 4281.
5. (d) Rossiter, B. E.; Katsuki, T. and Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 464.
6. (e) Mori, K.; Ebata, T. Tetrahedron. 1986, 42, 3471.
7. (f) Tsuboi, S.; Furutani, H.; Takeda, A.; Sato, S. Bull. Chem. Soc. Jpn. 1987, 60, 2475.
8. (g) Marczak, S.; Masnyk, M.; Wicha, J. Tetrahedron Lett. 1989, 30, 2845.
9. (h) Satoh, T.; Oohara, T.; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130.
10. (i) Kang, S.-K.; Kim, Y.-S.; Lim, J.-S.; Kim, K.-S.; Kim, S.-G. Tetrahedron Lett. 1991, 32, 363.
11. (j) Brevet, J.-L.; Mori, K. Synthesis 1992, 1007.
12. (k) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A.; Wang, Z.-M.; Zhang, X.-L.; Sharpless, K. B. Tetrahedron Lett. 1992, 33, 6411.
13. (l) Ko, S.Y. Tetrahedron Lett. 1994, 35, 3601.
14. (m) Paolucci, C.; Mazzini, C.; Fava, A. J. Org. Chem. 1995, 60, 169.
15. Tsuboi, S.; Furutani, H.; Takeda, A. Synthesis 1987, 292.
16. Chen, C.-S.; Fujimoto, Y.; Girdankar, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
17. Akita, H.; Enoki, Y.; Yamada, H.; Oishi, T. Chem. Pharm. Bull. 1989, 37, 2876.
18. Sugai, T.; Ohta, H. Agric. Biol. Chem. 1990, 54, 3337.
19. Akita, H.; Kawaguchi, T.; Enoki, Y.; Oishi, T. Chem. Pharm. Bull. 1990, 38, 323.
20. Lefker, B. A.; Hada, W. A.; McGarry, P. J. Tetrahedron Lett. 1994, 35, 5205.
21. Chadha, A.; Manohar, M. Tetrahedron: Asymmetry 1995, 6, 651.
22. Determination of syn-and anti-isomer was established by comparison of HPLC and spectral data with those of the literature (ref. 1). syn-Isomer eluted faster than the corresponding anti-isomer.
23. Enantiomeric excess was determined by HPLC analysis (column: Daicel Chiralcel OB-H (4.6 mm φ×250 mm), eluent: hexane/isopropanol (10/1), 0.5 ml/min).