Hydrolase-catalyzed preparation of (R)- and (S)-4-hydroxy-2,6,6- trimethyl-2-cyclohexen-1-ones (phorenols), the key synthetic intermediates for abscisic acid

Tetrahedron Asymmetry

Volumn 10, Issue 19, 1999, Pages 3811-3817

  Kiyota, Hiromasa ^a   Nakabayashi, Miho ^a   Oritani, Takayuki ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; ABSCISIC ACID; CAROTENOID; CHLOROACETIC ACID; ESTER DERIVATIVE; ESTERASE; HYDROLASE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033452451     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00391-2     Document Type: Article

References (31)

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19. Recent reviews, see: (a) Mori, K. Synlett. 1995, 1097-1109. (b) Theil, F. Chem. Rev. 1995, 95, 2203-2227. (c) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826. Roberts, S. M.; Williamson, N. M. Current Organic Chemistry 1997, 1, 1-20. (e) Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1608-1633.
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24. Recent examples of chloroacetate in enzymatic reactions, see: (a) Yonezawa, T.; Sakamoto, Y.; Nogawa, K.; Yamazaki T.; Kitazume, T. Chem. Lett. 1996, 855-856. (b) Kanerva, L. T.; Csomos, P.; Sundholm, O.; Bernath, G.; Fueloep, F. Tetrahedron: Asymmetry 1996, 7, 1705-1716. (c) Kato, K.; Katayama, M.; Fujii, S.; Fukaya, H.; Kimoto, H. J. Ferment. Bioeng. 1996, 81, 206-211. (d) Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. J. Org. Chem. 1996, 61, 8610-8616. (e) Kato, K.; Katayama, M.; Fujii, S.; Kimoto, H. Biosci. Biotechnol. Biochem. 1997, 61, 194-196. (f) Akeboshi, T.; Ohtsuka, Y.; Sugai, T.; Ohta, H. Tetrahedron 1998, 54, 7387-7394. (g) Ikeda, H.; Sugai, T.; Hosomi, H.; Ohba, S.; Ohta, H. Biosci. Biotechnol. Biochem. 1998, 62, 396-400.
25. Recent examples of chloroacetate in enzymatic reactions, see: (a) Yonezawa, T.; Sakamoto, Y.; Nogawa, K.; Yamazaki T.; Kitazume, T. Chem. Lett. 1996, 855-856. (b) Kanerva, L. T.; Csomos, P.; Sundholm, O.; Bernath, G.; Fueloep, F. Tetrahedron: Asymmetry 1996, 7, 1705-1716. (c) Kato, K.; Katayama, M.; Fujii, S.; Fukaya, H.; Kimoto, H. J. Ferment. Bioeng. 1996, 81, 206-211. (d) Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. J. Org. Chem. 1996, 61, 8610-8616. (e) Kato, K.; Katayama, M.; Fujii, S.; Kimoto, H. Biosci. Biotechnol. Biochem. 1997, 61, 194-196. (f) Akeboshi, T.; Ohtsuka, Y.; Sugai, T.; Ohta, H. Tetrahedron 1998, 54, 7387-7394. (g) Ikeda, H.; Sugai, T.; Hosomi, H.; Ohba, S.; Ohta, H. Biosci. Biotechnol. Biochem. 1998, 62, 396-400.
26. Recent examples of chloroacetate in enzymatic reactions, see: (a) Yonezawa, T.; Sakamoto, Y.; Nogawa, K.; Yamazaki T.; Kitazume, T. Chem. Lett. 1996, 855-856. (b) Kanerva, L. T.; Csomos, P.; Sundholm, O.; Bernath, G.; Fueloep, F. Tetrahedron: Asymmetry 1996, 7, 1705-1716. (c) Kato, K.; Katayama, M.; Fujii, S.; Fukaya, H.; Kimoto, H. J. Ferment. Bioeng. 1996, 81, 206-211. (d) Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. J. Org. Chem. 1996, 61, 8610-8616. (e) Kato, K.; Katayama, M.; Fujii, S.; Kimoto, H. Biosci. Biotechnol. Biochem. 1997, 61, 194-196. (f) Akeboshi, T.; Ohtsuka, Y.; Sugai, T.; Ohta, H. Tetrahedron 1998, 54, 7387-7394. (g) Ikeda, H.; Sugai, T.; Hosomi, H.; Ohba, S.; Ohta, H. Biosci. Biotechnol. Biochem. 1998, 62, 396-400.
27. Recent examples of chloroacetate in enzymatic reactions, see: (a) Yonezawa, T.; Sakamoto, Y.; Nogawa, K.; Yamazaki T.; Kitazume, T. Chem. Lett. 1996, 855-856. (b) Kanerva, L. T.; Csomos, P.; Sundholm, O.; Bernath, G.; Fueloep, F. Tetrahedron: Asymmetry 1996, 7, 1705-1716. (c) Kato, K.; Katayama, M.; Fujii, S.; Fukaya, H.; Kimoto, H. J. Ferment. Bioeng. 1996, 81, 206-211. (d) Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. J. Org. Chem. 1996, 61, 8610-8616. (e) Kato, K.; Katayama, M.; Fujii, S.; Kimoto, H. Biosci. Biotechnol. Biochem. 1997, 61, 194-196. (f) Akeboshi, T.; Ohtsuka, Y.; Sugai, T.; Ohta, H. Tetrahedron 1998, 54, 7387-7394. (g) Ikeda, H.; Sugai, T.; Hosomi, H.; Ohba, S.; Ohta, H. Biosci. Biotechnol. Biochem. 1998, 62, 396-400.
28. Recent examples of chloroacetate in enzymatic reactions, see: (a) Yonezawa, T.; Sakamoto, Y.; Nogawa, K.; Yamazaki T.; Kitazume, T. Chem. Lett. 1996, 855-856. (b) Kanerva, L. T.; Csomos, P.; Sundholm, O.; Bernath, G.; Fueloep, F. Tetrahedron: Asymmetry 1996, 7, 1705-1716. (c) Kato, K.; Katayama, M.; Fujii, S.; Fukaya, H.; Kimoto, H. J. Ferment. Bioeng. 1996, 81, 206-211. (d) Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. J. Org. Chem. 1996, 61, 8610-8616. (e) Kato, K.; Katayama, M.; Fujii, S.; Kimoto, H. Biosci. Biotechnol. Biochem. 1997, 61, 194-196. (f) Akeboshi, T.; Ohtsuka, Y.; Sugai, T.; Ohta, H. Tetrahedron 1998, 54, 7387-7394. (g) Ikeda, H.; Sugai, T.; Hosomi, H.; Ohba, S.; Ohta, H. Biosci. Biotechnol. Biochem. 1998, 62, 396-400.
29. Recent examples of chloroacetate in enzymatic reactions, see: (a) Yonezawa, T.; Sakamoto, Y.; Nogawa, K.; Yamazaki T.; Kitazume, T. Chem. Lett. 1996, 855-856. (b) Kanerva, L. T.; Csomos, P.; Sundholm, O.; Bernath, G.; Fueloep, F. Tetrahedron: Asymmetry 1996, 7, 1705-1716. (c) Kato, K.; Katayama, M.; Fujii, S.; Fukaya, H.; Kimoto, H. J. Ferment. Bioeng. 1996, 81, 206-211. (d) Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. J. Org. Chem. 1996, 61, 8610-8616. (e) Kato, K.; Katayama, M.; Fujii, S.; Kimoto, H. Biosci. Biotechnol. Biochem. 1997, 61, 194-196. (f) Akeboshi, T.; Ohtsuka, Y.; Sugai, T.; Ohta, H. Tetrahedron 1998, 54, 7387-7394. (g) Ikeda, H.; Sugai, T.; Hosomi, H.; Ohba, S.; Ohta, H. Biosci. Biotechnol. Biochem. 1998, 62, 396-400.
30. Recent examples of chloroacetate in enzymatic reactions, see: (a) Yonezawa, T.; Sakamoto, Y.; Nogawa, K.; Yamazaki T.; Kitazume, T. Chem. Lett. 1996, 855-856. (b) Kanerva, L. T.; Csomos, P.; Sundholm, O.; Bernath, G.; Fueloep, F. Tetrahedron: Asymmetry 1996, 7, 1705-1716. (c) Kato, K.; Katayama, M.; Fujii, S.; Fukaya, H.; Kimoto, H. J. Ferment. Bioeng. 1996, 81, 206-211. (d) Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. J. Org. Chem. 1996, 61, 8610-8616. (e) Kato, K.; Katayama, M.; Fujii, S.; Kimoto, H. Biosci. Biotechnol. Biochem. 1997, 61, 194-196. (f) Akeboshi, T.; Ohtsuka, Y.; Sugai, T.; Ohta, H. Tetrahedron 1998, 54, 7387-7394. (g) Ikeda, H.; Sugai, T.; Hosomi, H.; Ohba, S.; Ohta, H. Biosci. Biotechnol. Biochem. 1998, 62, 396-400.
31. Esterase SNSM-87 is available for laboratory use on request. Please contact the Research and Development Center, Nagase and Co. Ltd.; fax +81-78-992-1050.