Enantioselective synthesis of the alcohol moiety of dolabriferol

Journal of Organic Chemistry

Volumn 72, Issue 22, 2007, Pages 8484-8488

  Pelchat, Nicholas ^a   Caron, Dave ^a   Chênevert, Robert ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DOLABRIFEROL; ENZYMATIC DESYMMETRIZATION; PENTANETRIOL;

CHARACTERIZATION; ENANTIOSELECTIVITY; ESTERS; SYNTHESIS (CHEMICAL);

ALCOHOLS;

2,4 DIMETHYL 1,3,5 PENTANETRIOL; ALCOHOL DERIVATIVE; DOLABRIFEROL; PROPIONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ENANTIOSELECTIVITY; REACTION ANALYSIS; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR CONFORMATION; PENTANOLS; PYRANS; STEREOISOMERISM;

EID: 35548967170     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701524p     Document Type: Article

References (22)

1. Ciavatta, M. L.; Gavagnin, M.; Puliti, R.; Cimino, G.; Martinez, E.; Ortea, J.; Mattia, C. A. Tetrahedron 1996, 52, 12831-12838.
2. (a) Davies-Coleman, M. T.; Garson, M. J. Nat. Prod. Rep. 1998, 15, 477-493.
3. (b) Katz, L. Chem. Rev. 1997, 97, 2557-2575.
4. (a) Staunton, J.; Weissman, K. J. Nat. Prod. Rep. 2001, 18, 380-416.
5. (b) Rohr, J. Angew. Chem., Int. Ed. 2000, 39, 2847-2849.
6. Manker, D. C.; Faulkner, D. J.; Stout, T. J.; Clardy, J. J. Org. Chem. 1989, 54, 5371-5374.
7. Brecknell, D. J.; Collett, L. A.; Davies-Coleman, M. T.; Garson, M. J.; Jones, D. D. Tetrahedron 2000, 56, 2497-2502.
8. Socorro, I. M.; Taylor, K.; Goodman, J. M. Org. Lett. 2005, 7, 3541-3544.
9. Dias, L. C.; de Sousa, M. A. Tetrahedron Lett. 2003, 44, 5625-5628.
10. Chênevert, R.; Courchesne, G.; Caron, D. Tetrahedron: Asymmetry 2003, 14, 2567-2571.
11. Lister, T.; Perkins, M. V. Org. Lett. 2006, 8, 1827-1830.
12. (a) Koskinen, A. M. P.; Karisalmi, K.; Chem. Soc. Rev. 2005, 34, 677-690.
13. (b) Hoffmann, R. W. Angew. Chem., Int. Ed. 2003, 42, 1096-1109.
14. (c) Hoffman, R. W.; Dahmann, G.; Andersen, M. W. Synthesis 1994, 629-638.
15. Harada, T.; Inoue, A.; Wada, I.; Uchimura, J.; Tanaka, S.; Oku, A. J. Am. Chem. Soc. 1993, 115, 7665-7674.
16. Chênevert, R.; Courchesne, G. Tetrahedron: Asymmetry 1995, 6, 2093-2096.
17. (a) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc. 1996, 118, 4322-4343.
18. (b) Reetz, M. T.; Kesseler, K.; Jung, A. Tetrahedron Lett. 1984, 25, 729-732.
19. Lautens, M.; Stammers, T. A. Synthesis 2002, 14, 1993-2012.
20. (a) Garcia-Urdiales, E.; Alfonso, I.; Gotor, V. Chem. Rev. 2005, 105, 313-354.
21. (b) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826.
22. Domon, L.; Vogeleisen, F.; Uguen, D. Tetrahedron Lett. 1996, 37, 2773-2776.