Synthesis and enzymatic cyclization of (3S)-14-fluoro-2,3-oxidosqualene

Tetrahedron Letters

Volumn 39, Issue 51, 1998, Pages 9385-9388

  Robustell, Brian J ^a   Abe, Ikuro ^b,c   Prestwicht, Glenn D ^b  

^a STONY BROOK UNIVERSITY   (United States)

^b UNIVERSITY OF UTAH   (United States)

^c UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

14 FLUORO 2,3 OXIDOSQUALENE; SQUALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; CYCLIZATION; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME SUBSTRATE COMPLEX;

EID: 0032542159     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02197-2     Document Type: Article

References (25)

1. 1. For a review, see: Abe, I.; Rohmer, M.; Prestwich, G. D. Chem. Rev. 1993, 93, 2189.
2. 2. For vertebrate OSLCs, (a) Abe, I.; Bai, M.; Xiao, X.-y.; Prestwich, G. D. Biochem. Biophys. Res. Commun. 1992, 187, 32 (purification);
3. (b) Abe, I.; Prestwich, G. D. Proc. Natl. Acad. Sci. USA 1995, 92, 9274 (cloning and expression).
4. 3. For A. acidocaldarius SHC: (a) Ochs, D.; Tappe, C. H.; Gärtner, P.; Kellner, R.; Poralla, K. Eur. J. Biochem. 1990, 194, 75 (purification);
5. (b) Ochs, D.; Kaletta, C.; Entian, K.-D.; Beck-Sickinger, A.; Poralla, K. J. Bacteriaol. 1992, 174, 298 (cloning and expression).
6. 4. Wendt, K.-U.; Poralla, K.; Schultz, G. E. Science 1997, 277, 1811.
7. 5. Robustell, B.; Abe, I.; Prestwich, G. D. Tetrahedron Lett. 1998, 39, 957.
8. 6. (a) Johnson, W. S.; Chenera, B.; Tham, F. S.; Kullnig, R. K. J. Am. Chem. Soc. 1993, 115, 493;
9. (b) Johnson, W. S.; Fletcher, V. R.; Chenera, B.; Bartlett, W. R.; Tham, F. S.; Kullnig, R. K. J. Am. Chem. Soc. 1993, 115, 497;
10. (c) Johnson, W. S.; Buchanan, R. A.; Bartlett, W. R.; Tham, F. S.; Kullnig, R. K. J. Am. Chem. Soc. 1993, 115, 504;
11. (d) Johnson, W. S.; Plummer, M. S.; Reddy, S. P.; Bartlett, W. R. J. Am. Chem. Soc. 1993, 115, 515.
12. 7. Robustell B. J., Ph.D. Dissertation, State University of New York at Stony Brook, Stony Brook, New York, 1998.
13. 8. (a) Wang, L.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7568.
14. (b) Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7570.
15. (c) Crispino, G. A.; Sharpless, K. B. Tetrahedron Lett. 1992, 33, 4273.
16. 49FO: calcd 444.3762; found, 444.3756.
17. f = 0.18).
18. 1H-NMR data are available for this manuscript by contacting the authors.
19. (d) An inseparable mixture of racemic 11-and 14-FOS regioisomers was first chemically synthesized from 11-fluorosqualene: Xiao, X.-y. Ph.D. Dissertation, State University of New York at Stony Brook, Stony Brook, New York, 1991.
20. 10. Similar results have been observed for the cyclization of oxidosqualene and its derivatives by bacterial squalene cyclase. See: (a) Rohmer, M.; Anding, C.; Ourisson, G. Eur. J. Biochem. 1980, 112, 541;
21. (b) Rohmer, M.; Bouvier, P.; Ourisson, G. Eur. J. Biochem. 1980, 112, 557;
22. (c) Bouvier, P.; Berger, Y.; Rohmer, M.; Ourisson, G. Eur. J. Biochem. 1980, 112, 549;
23. (d) Abe, I.; Rohmer, M. J. Chem. Soc. Perkin Trans. 1 1994, 783.;
24. (e) Abe, I.; Dang, T.; Zheng, Y. F.; Madden, B. A., Feil, C.; Poralla, K.; Prestwich, G. D. J. Am. Chem. Soc. 1997, 119, 11333;
25. (f) Zheng, Y. F.; Abe, I.; Prestwich, G. D. J. Org. Chem. 1998, 63, 4872.