Chemoenzymatic synthesis of the microbial elicitor (-)-syringolide via a fructose 1,6-diphosphate aldolase-catalyzed condensation reaction

Journal of Organic Chemistry

Volumn 65, Issue 15, 2000, Pages 4529-4531

  Chênevert, Robert ^a   Dasser, Mohammed ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

FRUCTOSE BISPHOSPHATE ALDOLASE; SYRINGOLIDE; UNCLASSIFIED DRUG; VEGETABLE PROTEIN;

ARTICLE; POLYMERIZATION; PSEUDOMONAS SYRINGAE; REACTION ANALYSIS; SOYBEAN; SYNTHESIS; TOMATO;

ALKYLATION; ANIMALS; ANTI-BACTERIAL AGENTS; FRUCTOSE-BISPHOSPHATE ALDOLASE; HETEROCYCLIC COMPOUNDS, 3-RING; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MUSCLE, SKELETAL; PLANT DISEASES; PSEUDOMONAS; RABBITS; SESQUITERPENES; STEREOISOMERISM;

EID: 0343962581     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991989e     Document Type: Article

References (23)

1. Schröder, F. Angew. Chem., Int. Ed. 1998, 37, 1213.
2. Midland, S. L.; Keen, N. T.; Sims, J. J.; Midland, M. M.; Stayton, M. M.; Burton, V.; Smith, M. J.; Mazzola, E. P.; Graham, K. J.; Clardy, J. J. Org. Chem. 1993, 58, 2940.
3. (a) Henschke, J. P.; Rickards, R. W. Tetrahedron Lett. 1996, 37, 3557.
4. (b) Zeng, C. M.; Midland, S. L.; Keen, N. T.; Sims, J. J. J. Org. Chem. 1997, 62, 4780.
5. (c) Yoda, H.; Kawauchi, M.; Takabe, K.; Hosoya, K. Heterocycles 1997, 45, 1895.
6. (d) Kuwahara, S.; Moriguchi, M.; Miyagawa, K.; Konno, M.; Kodama, O. Tetrahedron 1995, 51, 8809.
7. (e) Wood, J. L.; Jeong, S.; Salcedo, A.; Jenkins, J. J. Org. Chem. 1995, 60, 286.
8. (f) Yu, P.; Wang, Q. G.; Mak, T. C. W.; Wong, H. N. C. Tetrahedron 1998, 54, 1783.
9. (g) Ishihara, J.; Sugimoto, T.; Murai, A. Tetrahedron 1997, 53, 16029.
10. (h) Honda, T.; Mizutani, H.; Kanai, K. J. Org. Chem. 1996, 61, 9374.
11. (a) Schoevaart, R.; van Rantwijk, F.; Sheldon, R. A. Tetrahedron: Asymmetry 1999, 10, 705.
12. (b) Fessner, W. D. Current Opin. Chem. Biol. 1998, 2, 85.
13. (c) Takayama, S.; McGarney, G. J.; Wong, C. H. Chem. Soc. Rev. 1997, 26, 407.
14. (a) Schultz, M.; Waldmann, H.; Vogt, W.; Kunz, H. Tetrahedron Lett. 1990, 31, 867.
15. (b) Chênevert, R.; Lavoie, M.; Dasser, M.; Can. J. Chem. 1997, 75, 68.
16. (e) Shimagaki, M.; Muneshima, H.; Kubota, M.; Oishi, T. Chem. Pharm. Bull. 1993, 41, 282.
17. (d) Malleron, A.; David, S. New J. Chem. 1996, 20, 153.
18. (a) England, P.; Chun, K. H.; Moran, E. J.; Armstrong, R. W. Tetrahedron Lett. 1990, 31, 2669.
19. (b) Kwart, H.; Sarner, S. F.; Slutsky, J. J. Org Chem. 1973, 38, 5234.
20. Jung, S. H.; Jeong, J. H.; Miller, P.; Wong, C. H. J. Org. Chem. 1994, 59, 7182.
21. (a) Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; Chapter 4, pp 195-251.
22. (b) Kaber, K.; Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995; Chapter 2, pp 219-235.
23. Oikawa, Y.; Sugano, K.; Yonemitsu, O. J. Org. Chem. 1978, 43, 2087.