Preparation of 3-alkyl-4-hydroxy-2-butenyl acetate through highly regioselective lipase-catalyzed hydrolysis of corresponding diacetates

Tetrahedron Letters

Volumn 37, Issue 1, 1996, Pages 91-92

  Itoh, Toshiyuki ^a   Uzu, Ayako ^a   Kanda, Naoki ^a   Takagi, Yumiko ^b  

^a OKAYAMA UNIVERSITY   (Japan)

^b HYOGO UNIVERSITY OF TEACHER EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID ESTER; ALKANEDIOL DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; DRUG SYNTHESIS; ENZYME ACTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030046187     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02111-6     Document Type: Article

References (8)

1. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry, Pergamon, Oxford, 1994.
2. For recent examples see: (a) Palmer, D. C.; Terradas, F. Tetrahedron Lett. 1994, 35, 1673.
3. (b) Morimoto, T.; Murakami, N.; Nagata, A.; Sakakibara, J. Pharm. Bull. 1994, 47, 751.
4. (c) Danieli, B.; Luisetti, M.; Riva, S.; Bertinotti, A.; Ragg, E.; Scaglioni, L.; Bombardelli, E. J. Org.Chem., 1995, 60, 3637.
5. Four other types of enzymes can hydrolyze 1a preferentially at the 1-position giving monoacetate in ca.60% yield with more than 70% regioselectivity; PL (Meito, Alcaligenes sp., 90% at 0°C for 8h), Porcine Pancreatin (Sigma Type II, 89% at 0°C for 336 h). PS (Amano, Pseudomonas cepacia, 86% at 0°C for 4 h), OF (Meito, Candida cylindracea, 73% at 0°C for 0.75 h).
6. Diacetate 1a was prepared from 2-methyl-1,3-butadiene; Oroshnik, W.; Mallory, R. A. J. Am. Chem. Soc., 1950, 72, 4608.
7. Sato, F.; Kobayashi, Y. Org.Synth. Coll. Vol VIII, 1993, 507.
8. The authors are grateful to Professors Kenji Uneyama and Takashi Sakai of Okayama University for their valuable discussions throughout this work. They also grateful to the SC-NMR Laboratory of Okayama University for the NMR measurements.