An aldol-based approach to the asymmetric synthesis of L-Callipeltose, the deoxyamino sugar of L-Callipeltoside A

Organic Letters

Volumn 3, Issue 20, 2001, Pages 3133-3136

  Evans, David A ^a   Hu, Essa ^a   Tedrow, Jason S ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOSUGAR; ANTIINFECTIVE AGENT; ANTINEOPLASTIC ANTIBIOTIC; CALLIPELTOSE; CALLIPELTOSIDE A; MACROLIDE; THREONINE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINO SUGARS; ANTI-BACTERIAL AGENTS; ANTIBIOTICS, ANTINEOPLASTIC; MACROLIDES; STEREOISOMERISM; THREONINE;

EID: 0035807581     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016416e     Document Type: Article

References (24)

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. Tetrahedron 1997, 53, 3243-3248.
3. Our synthesis of the side chain has been published: Evans, D. A.; Burch, J. D. Org. Lett. 2001, 3, 503-505.
4. (a) Smith, G. R.; Finley, J. J. IV; Giuliano, R. M. Carbohydr. Res. 1998, 308, 223-237.
5. (b) Gurjar, M. K.; Reddy, R. Carbohydrate Lett. 1998, 3, 169-172.
6. Pihko, A. J.; Nicolaou, K. C.; Koskinen, A. M. P. Tetrahedron: Asymmetry 2001, 12, 937-942.
7. Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesmi, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461-5464.
8. Other conditions and nucleophiles, such as methyllithium, lead to lower yields.
9. (a) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1987, 52, 1353-1355.
10. (b) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1987, 52, 3176-3178.
11. Pearson, W. H.; Hines, J. V. J. Org. Chem. 1989, 54, 4235-4237.
12. Comins, D. L.; Kuethe, J. T.; Lakner, F. J. J. Am. Chem. Soc. 1999, 121, 2651-2652.
13. One of our referees pointed out that the surname ot author "Nguyen Trong Anh" is actually Nguyen because surnames are listed first according to Vietnamese custom. Therefore, we will refer to the polar model as the Felkin-Nguyen model instead of the Felkin-Anh model. (a) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
14. (b) Nguyen, T. A.; Eisenstein, O. Nouv. J. Chim. 1977, 1, 61-70.
15. Nguyen, T. A. Top. Curr. Chem. 1980, 88, 146-162.
16. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920-1923.
17. For a discussion of (Z) enolate additions to chiral substituted aldehydes, see: (a) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1-115.
18. (b) Roush, W. R. J. Org. Chem. 1991, 56, 4151-4157.
19. Heathcock, C. H.; Young, S. D.; Hagan, J. P.; Pirrung, M. C.; White, C. T.; VanDerveer, D. J. Org. Chem. 1980, 45, 3846-3856.
20. Evans, D. A.; Trotter, B. W.; Coleman, P. J.; Cote, B.; Dias, L. C.; Rajapakse, H. A.; Tyler, A. N. Tetrahedron 1999, 55, 8671-8726.
21. (a) Dahanukar, V. H.; Rychnovsky, S. D. J. Org. Chem. 1996, 61, 8317-8320.
22. (b) Kopecky, D. J.; Rychnovsky, S. D. J. Org. Chem. 2000, 65, 191-198.
23. Benzyl acetate was a major byproduct in the reaction mixture, supporting the proposed role of benzyl alkoxide in acetate cleavage.
24. Sebesta, D. P.; Roush, W. R. J. Org. Chem. 1992, 57, 4799-4802.