Chemo-enzymatic synthesis of (-)-epipentenomycin I

Tetrahedron Asymmetry

Volumn 14, Issue 24, 2003, Pages 3885-3889

  Klomklao, Tawesin ^a   Pyne, Stephen G ^b   Baramee, Apiwat ^a   Skelton, Brian W ^c   White, Allan H ^c  

^a CHIANG MAI UNIVERSITY   (Thailand)

^b UNIVERSITY OF WOLLONGONG   (Australia)

^c UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXY 5 METHYLENE 2 CYCLOPENTENONE; ALCOHOL; ANTIINFECTIVE AGENT; CYCLOPENTENONE DERIVATIVE; DIMETHYLDIOXIRANE; ENZYME; EPIPENTENOMYCIN I; EPOXIDE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; EPOXIDATION; HYDROLYSIS; PRIORITY JOURNAL; PYROLYSIS; RING OPENING; VACUUM;

EID: 0345059173     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.10.003     Document Type: Article

References (23)

1. Umino K., Furumai T., Matsuzawa N., Awataguchi Y., Ito Y., Okuda T. J. Antibiot. 26:1973;506.
2. Shomura T., Hoshida J., Kondo Y., Watanabe H., Omoto S., Inouye S., Niida T. Kenyu Nempo. 16:1976;1.
3. Bernillon J., Bonvin J.F., Pommier M.T., Arpin N. J. Antibiot. 13:1989;1430.
4. Baute M.-A., Deffieux G., Baute R., Badoc A., Vercauteren J., Leger J.-M., Neveu A. Phytochem. 30:1991;1419.
5. Smith A.B. III, Pilla N.N. Tetrahedron Lett. 21:1980;4691.
6. Shono T., Matsumura Y., Yamane S., Suzuki M. Chem. Lett. 1980;1619.
7. Elliott J.D., Hetmanski M., Palfreyman M.N., Purcell N., Stoodley R.J. Tetrahedron Lett. 24:1983;965.
8. Hetmanski M., Purcell N., Stoodley R.J., Palfreyman M.N. J. Chem. Soc., Perkin Trans. 1. 1984;2089.
9. Sugahara T., Ogasawara K. Synlett. 1999;419.
10. Seepersaud M., Al-Abed Y. Tetrahedron Lett. 41:2000;4291.
11. Gallos J.K., Damianou K.C., Dellios C.C. Tetrahedron Lett. 42:2001;5769.
12. Smith A.B. III, Branca S.J., Pilla N.N., Guaciaro M.A. J. Org. Chem. 47:1982;1855.
13. Pohmakotr M., Popuang S. Tetrahedron Lett. 32:1991;275.
14. Phutdhawong W., Pyne S.G., Baramee A., Buddhasukh D., Skelton B.W., White A.H. Tetrahedron Lett. 43:2002;6047.
15. Verlaak J.M.J., Klunder A.J.H., Zwanenburg B. Tetrahedron Lett. 23:1982;5463.
16. Klunder A.J.H., Houwen-Claassen A.A.M., Kooy M.G., Zwanenburg B. Tetrahedron Lett. 28:1987;1329.
17. Houwen-Claassen A.A.M., Klunder A.J.H., Zwanenburg B. Tetrahedron. 45:1989;7134.
18. Chantarasiri N., Dinprasert P., Thebtaranonth C., Thebtaranonth Y., Yenjai C. J. Chem. Soc., Chem. Commun. 1990;286.
19. o=1176 (CCDC# 212132). The chirality adopted is assigned from chemistry. The material was 'difficult', presumably in consequence of the packing of the molecules in strings, each made up of symmetry-related sequences of the independent components molecule 1 or molecule 2 of the asymmetric unit, linked by hydrogen-bonds between the hydroxyl hydrogen of one molecule and the ketonic oxygen of the next.
20. The percentage conversion was calculated from the enantiomeric excess of the starting alcohol 8 and acetate 9 according to % conv.=68/(68+98)=41. See: Chen C.-S., Fujimoto Y., Girdaukas G., Sih C.J. J. Am. Chem. Soc. 104:1982;7294.
21. Murray R.W., Singh M. Org. Synth. 74:1997;91.
22. For the ring-opening of an epoxide with water, see: Lubineau A., Billault I. Carbohydr. Res. 320:1999;49.
23. Yenji, C. Ph.D. thesis (Organic Chemistry), Department of Chemistry, Mahidol University, 1989.