Organosilanes in synthesis: Application to an enantioselective synthesis of methyl-L-callipeltose

Organic Letters

Volumn 5, Issue 11, 2003, Pages 1991-1993

  Huang, Hongbing ^a   Panek, James S ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDEHYDE; ALLYLSILANE 6; CARBOHYDRATE; CHROMIUM; LACTONE; METHYL CALLIPELTOSE; SILANE DERIVATIVE; UNCLASSIFIED DRUG; AMINOSUGAR; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; CALLIPELTOSIDE A; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; MACROLIDE; METHYL L CALLIPELTOSE; METHYL-L-CALLIPELTOSE;

ARTICLE; CATALYSIS; CHEMICAL BOND; ENANTIOSELECTIVITY; OXIDATION; QUANTUM YIELD; SYNTHESIS; ANIMAL; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPONGE (PORIFERA); STEREOISOMERISM;

AMINO SUGARS; ANIMALS; ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; CATALYSIS; CHROMIUM; INDICATORS AND REAGENTS; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; PORIFERA; SILANES; STEREOISOMERISM;

EID: 0042853247     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034582b     Document Type: Article

References (25)

1. (a) Zampella, A.; D'Auria, M. V.; Minale, L.; Debitus, C.; Roussakis, C. J. Am. Chem. Soc. 1996, 118, 11085-11088.
2. (b) Zampella, A.; D'Auria, M. V.; Minale, L.; Debitus, C.; Roussakis, C. Tetrahedron 1997, 53, 3243-3248.
3. (a) Trost, B. M.; Dirat, O.; Gunzner, J. L. Angew. Chem., Int. Ed. 2002, 41, 841-843.
4. (b) Trost, B. M.; Gunzner, J. L.; Dirat, O.; Rhee, Y. H. J. Am. Chem. Soc. 2002, 124, 10396-10415.
5. (c) Evans, D. A.; Hu, E; Burch, J. D.; Jaeschke, G. J. Am. Chem. Soc. 2002, 124, 5654-5655.
6. Smith, G. R.; Finley, J. J., IV; Giuliano, R. M. Carbohydr. Res. 1998, 308, 223-237.
7. Gurjar, M. K.; Reddy, R. Carbohydr. Lett. 1998, 3, 169-172.
8. Pihko, A. J.; Nicolaou, K. C.; Koskinen, A. M. P. Tetrahedron: Asymmetry 2001, 12, 937-942.
9. Evans, D. A.; Hu, E.; Tedrow, J. S. Org. Lett. 2001, 3, 3133-3136. For a racemic synthesis of methyl callipeltose, see 2b.
10. (a) Huang, H.; Panek, J. S. J. Am. Chem. Soc. 2000, 122, 9836-9837.
11. (b) Huang, H.; Panek, J. S. Org. Lett. 2001, 3, 1693-1696.
12. Chauret, D. C.; Chong, J. M.; Ye Q. Tetrahedron: Asymmetry 1999, 10, 3601-3614.
13. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
14. Enantiomeric excess (ee) analysis was conducted by chiral HPLC analysis.
15. Peterson, D. J. J. Org. Chem. 1968, 33, 780-784.
16. Stereochemistry of 8 was determined by NOE experiment. The cis stereoselectivity is consistent with our previous reported observations. For a discussion of the related transition state, see ref 7.
17. Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136-6137.
18. (a) Muzart, J.; Piva, O. Tetrahedron Lett. 1988, 29, 2321-2324.
19. (b) Chidambaram, N.; Chandrasekaran, S. J. Org. Chem. 1987, 52, 5048-5051.
20. (c) Pearson, A. J.; Chen, Y.; Han, G. R.; Hsu, S.; Ray, T. J. Chem. Soc., Perkin Trans. 1 1985, 267-273.
21. Zhao, M.; Li, J.; Song, Z.; Desmond, R.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron Lett. 1998, 39, 5323-5326.
22. Study on the mechanism, scope, and limitation of this novel reaction will be reported elsewhere. For a leading reference on Cr(VI)-catalyzed oxidation of the C-H bond, see: Lee, S.; Fuchs, P. L. J. Am. Chem. Soc. 2002, 124, 13978-13979.
23. (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
24. (b) Stereochemistry of 13 was determined by NOE experiment, see Supporting Information for detail.
25. Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598-600.