Chemoenzymatic synthesis of a versatile cyclopentenone: (+)-(3aS,6aS)-2,2-dimethyl-3aβ,6aβ-dihydro-4H-cyclopenta-1,3-dioxol- 4-one

Tetrahedron Asymmetry

Volumn 7, Issue 8, 1996, Pages 2313-2320

  Biadatti, Thibaud ^a   Esker, John L ^a   Johnson, Carl R ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; CYCLOPENTENONE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENZYME ACTIVITY; PRIORITY JOURNAL; PSEUDOMONAS; REACTION ANALYSIS;

EID: 0030220985     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00286-8     Document Type: Article

References (16)

1. 1. Johnson, C. R.; Penning, T. D. J. Am. Chem. Soc. 1986, 108, 5655.
2. 2. (a) Medich, J. R.; Kunnen, K.; Johnson, C. R. Tetrahedron Lett. 1987, 28, 4131;
3. (b) Johnson, C.R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854.
4. 3. Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 4, 313.
5. 4. (a) Ohrui, H.; Konno, M.; Meguro, H. Agric. Biol Chem. 1987, 51, 625;
6. (b) Belanger, P.; Prasit, P. Tetrahedron Lett. 1988, 29, 5521;
7. (c) Deardorff, D. R.; Shambayate, S.; Myles, D. C.; Heerding, D. J. Org. Chem. 1988, 53, 3614;
8. (d) Johnson, C. R.; Penning, T. D. J. Am. Chem. Soc. 1988, 110, 4726;
9. (e) Ali, S. M.; Ramesh, K.; Borchardt, R. T. Tetrahedron Lett. 1990, 31, 1509;
10. (f) Hudlicky, T.; Natchus, M. G.; Nugent, T. C. Synth. Commun. 1992, 22, 151.
11. 5. Siddiqi, S. M.; Schneller, S. W.; Ikeda. S.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. Nucleosides Nucleotides 1993, 12, 185.
12. 6. Johnson, C. R.; Nerurkar, B. M.; Golebiowski, A.; Sundram, H.; Esker, J. L. J. Chem. Soc., Chem. Commun. 1995, 1139.
13. 7. The spectral data provide an easy method of identification of the minor and the major product of the reaction. The signals for the two olefinic protons coincide in the major components 2a and 2b (6.12-6.16 ppm and 6.13 ppm, respectively), indicating a sense of symmetry absent in the minor components, in which either of the olefinic proton has a distinct chemical shift..
14. 8. Petitou, M.; Duchaussoy, P.; Choay, J. Tetrahedron Lett. 1988, 29, 1389.
15. 20 +188 (c 1.0, acetone)) can significantly alter the observed rotation. Chiral HPLC analysis shows the crude phenoxy acetate (-)-3 to be 95 to 97% ee, and indicates that the vic-phenoxy acetate, both enantiomers of the phenoxy acetate 3 and traces of phenol are contained only in the mother liquor.
16. 10. The phenoxy alcohol 2b does not have sufficient solubility in the hexanes:isopropenyl acetate system that was used for the enzymatic resolution of the phenoxy alcohol 2a. Therefore the system isopropenyl acetate:acetonitrile was chosen, in which the amount of acetonitrile used is the minimal amount required to achieve dissolution of the substrate and maintain a comparable substrate concentration