Aluminum- and boron-mediated C-glycoside synthesis from 1,2-anhydroglycosides

Organic Letters

Volumn 2, Issue 17, 2000, Pages 2707-2709

  Rainier, Jon D ^a   Cox, Jason M ^a  

^a UNIVERSITY OF ARIZONA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM; BORON; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; EPOXIDE; GLYCOSIDE;

ARTICLE; CHEMISTRY; SYNTHESIS; TEMPERATURE;

ALUMINUM; BORON; EPOXY COMPOUNDS; GLYCOSIDES; INDICATORS AND REAGENTS; TEMPERATURE;

EID: 0034710476     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006286u     Document Type: Article

References (24)

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2. (b) Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton, Florida, 1995.
3. For anti-selective epoxide openings, see ref 3 and (a) Klein, L. L.; McWhorter, W. W., Jr.; Ko, S. S.; Pfaff, K.-P.; Kishi, Y.; Uemura, D.; Hirata, Y. J. Am. Chem. Soc. 1982, 104, 7362.
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7. (e) Guo, J. S.; Duffy, K. J.; Stevens, K. L.; Dalko, P. I.; Roth, R. M.; Hayward, M. M.; Kishi, Y. Angew. Chem., Int. Ed. 1998, 37, 187.
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9. (g) Evans, D. A.; Trotter, B. W.; Coleman, P. J.; Côté, B.; Dias, L. C.; Rajapakse, H. A.; Tyler, A. N. Tetrahedron 1999, 55, 8671.
10. (a) Rainier, J. D.; Allwein, S. P. J. Org. Chem. 1998, 63, 5310.
11. (b) Rainier, J. D.; Allwein, S. P. Tetrahedron Lett. 1998, 39, 9601.
12. (a) Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661.
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14. Rainier, J. D.; Allwein, S. P.; Cox, J. M. Org. Lett. 2000, 2, 231.
15. We are aware of one other report of the addition of trimethyl aluminum to glycal epoxides giving the product from syn-facial epoxide opening. See Bailey, J. M.; Craig, D.; Gallagher, P. T. Synlett 1999, 132.
16. 2 see: Leeuwenburgh, M. A.; Timmers, C. M.; van der Marel, G. A.; van Boom, J. H.; Mallet, J.-M.; Sinay, P. G. Tetrahedron Lett. 1997, 38, 6251.
17. 4), and concentrated. Flash chromatography (5:1 hexanes: ethyl acetate) afforded 44 mg (82%) of alcohol 6 as a colorless oil.
18. 1,2 ranged from 9.2 to 10 Hz. (a) ref 3.
19. 1,2 ranged from 4.2 to 5.9 Hz.
20. We have been unable to generate the corresponding β-alkynyl glycoside from the addition of acetylide anions to 4. Van Boom has generated α-alkynyl glycosides from alkynyl zinc additions. See ref 7.
21. 3) with the appropriate Grignard or lithium reagent. See: Paley, R. S.; Snow, S. R. Tetrahedron Lett. 1990, 31, 5853.
22. 4), and concentrated. Flash chromatography (5:1 hexanes:ethyl acetate) afforded 42 mg (76%) of alcohol 8 as a colorless oil.
23. We believe that the intermolecular addition is occurring from an aluminum "ate" complex (possibly chlorotriallyl aluminate). Thus far, we have not been able to purify triallyl aluminum.
24. Brown, H. C.; Racherla, U. S. J. Org. Chem. 1986, 51, 427.