A unified approach to the enantioselective synthesis of 2,6-cis and trans disubstituted tetrahydropyranones

Heterocycles

Volumn 62, Issue , 2004, Pages 179-183

  Crimmins, Michael T ^a   Diaz, Caroline J ^a   Emmitte, Kyle A ^a  

^a The University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROPYRAN DERIVATIVE; TETRAHYDROPYRANONE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; ENANTIOSELECTIVITY; ISOMERISM; KINETICS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0346459968     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. Isolation: J. Tanaka and T. Higa, Tetrahedron Lett., 1996, 37, 5535. Synthesis: A. B. Smith, I. G. Safonov, and R. M. Corbett, J. Am. Chem. Soc., 2002, 124, 11102.
2. Isolation: J. Tanaka and T. Higa, Tetrahedron Lett., 1996, 37, 5535. Synthesis: A. B. Smith, I. G. Safonov, and R. M. Corbett, J. Am. Chem. Soc., 2002, 124, 11102.
3. Isolation: B. Kunze, R. Jansen, F. Sasse, G. Hofle, and H. Reichenbach, J. Antibiot., 1998, 51, 1075. Synthesis: A. B +hattacharjee, O. R. Seguil, and J. K. De Brabander, Tetrahedron Lett., 2001, 42, 1217. A. Lewis, I. Stefanuti, S. A. Swain, S. A. Smith, and R. J. K. Taylor, Org. Biomol. Chem., 2003, 1, 104. K. C. Nicolaou, D. W. Kim, and R. Baati, Angew. Chem. Int. Ed., 2002, 41, 3701.
4. Isolation: B. Kunze, R. Jansen, F. Sasse, G. Hofle, and H. Reichenbach, J. Antibiot., 1998, 51, 1075. Synthesis: A. B +hattacharjee, O. R. Seguil, and J. K. De Brabander, Tetrahedron Lett., 2001, 42, 1217. A. Lewis, I. Stefanuti, S. A. Swain, S. A. Smith, and R. J. K. Taylor, Org. Biomol. Chem., 2003, 1, 104. K. C. Nicolaou, D. W. Kim, and R. Baati, Angew. Chem. Int. Ed., 2002, 41, 3701.
5. Isolation: B. Kunze, R. Jansen, F. Sasse, G. Hofle, and H. Reichenbach, J. Antibiot., 1998, 51, 1075. Synthesis: A. B +hattacharjee, O. R. Seguil, and J. K. De Brabander, Tetrahedron Lett., 2001, 42, 1217. A. Lewis, I. Stefanuti, S. A. Swain, S. A. Smith, and R. J. K. Taylor, Org. Biomol. Chem., 2003, 1, 104. K. C. Nicolaou, D. W. Kim, and R. Baati, Angew. Chem. Int. Ed., 2002, 41, 3701.
6. Isolation: B. Kunze, R. Jansen, F. Sasse, G. Hofle, and H. Reichenbach, J. Antibiot., 1998, 51, 1075. Synthesis: A. B +hattacharjee, O. R. Seguil, and J. K. De Brabander, Tetrahedron Lett., 2001, 42, 1217. A. Lewis, I. Stefanuti, S. A. Swain, S. A. Smith, and R. J. K. Taylor, Org. Biomol. Chem., 2003, 1, 104. K. C. Nicolaou, D. W. Kim, and R. Baati, Angew. Chem. Int. Ed., 2002, 41, 3701.
7. M. Murata, S. Matsuoka, N. Matsumori, G. K. Paul, and K. Tachibana, J. Am. Chem. Soc., 1999 121, 870.
8. Isolation: A. Cutignano, I. Bruno, G. Bifulco, A. Casapullo, C. Debitus, L. Gomez-Paloma, and R. Riccio, Eur. J. Org. Chem., 2001, 775. Synthesis: A. B. Smith and I. G. Safonov, Org. Lett., 2002, 4, 635.
9. Isolation: A. Cutignano, I. Bruno, G. Bifulco, A. Casapullo, C. Debitus, L. Gomez-Paloma, and R. Riccio, Eur. J. Org. Chem., 2001, 775. Synthesis: A. B. Smith and I. G. Safonov, Org. Lett., 2002, 4, 635.
10. M. A. Gonzalez and G. Pattenden, Angew. Chem. Int. Ed., 2003, 42, 1258 and references therein.
11. N. A. Petasis and S.-P. Lu, Tetrahedron Lett., 1996, 37, 141. A. B. Smith, P. R. Verhoest, K. P. Minbiole, and J. L. Lim, Org. Lett., 1999, 1, 909. A. B. Smith, K. P. Minbiole, P. R. Verhoest, and T. Beauchamp, Org. Lett., 1999, 1, 913.
12. N. A. Petasis and S.-P. Lu, Tetrahedron Lett., 1996, 37, 141. A. B. Smith, P. R. Verhoest, K. P. Minbiole, and J. L. Lim, Org. Lett., 1999, 1, 909. A. B. Smith, K. P. Minbiole, P. R. Verhoest, and T. Beauchamp, Org. Lett., 1999, 1, 913.
13. N. A. Petasis and S.-P. Lu, Tetrahedron Lett., 1996, 37, 141. A. B. Smith, P. R. Verhoest, K. P. Minbiole, and J. L. Lim, Org. Lett., 1999, 1, 909. A. B. Smith, K. P. Minbiole, P. R. Verhoest, and T. Beauchamp, Org. Lett., 1999, 1, 913.
14. (a) M. T. Crimmins and K. A. Emmitte, Org. Lett., 1999, 1, 2029.
15. (b) M. T. Crimmins and K. A. Emmitte, Synthesis, 2000, 899.
16. (c) M. T. Crimmins, K. A. Emmitte, and A. L. Choy, Tetrahedron, 2002, 58, 1817.
17. (d) M. T. Crimmins, M. G. Stanton, and S. P. Allwein, J. Am. Chem. Soc., 2002, 124, 5958.
18. (e) M. T. Crimmins and M. T. Powell, J. Am. Chem. Soc., 2003, 125, 7592.
19. (f) M. T. Crimmins and K. A. Emmitte, J. Am. Chem. Soc., 2001, 123, 1533.
20. For representative examples of tetrahydropyranones in total synthesis see: L.-S. Li, Y.-L. Wu, and Y. Wy,Org. Lett., 2000, 2, 891. D. L. Wright, L. C. Usher, and M. Estralla-Jimenez, Org. Lett., 2001, 3, 4275. D. A. Evans, P. H. Carter, E. M. Carreira, A. B. Charette, J. A. Prunet, and M. Lautens, J. Am. Chem. Soc., 1999, 121, 7540. D. A. Evans, D. M. Fitch, T. E. Smith, and B. J. Cee, J. Am. Chem. Soc., 2000, 122, 10033. T. P. Loh, J. Y. Yang, L. C. Feng, and Y. Zhou, Tetrahedron Lett., 2002, 43, 7193.
21. For representative examples of tetrahydropyranones in total synthesis see: L.-S. Li, Y.-L. Wu, and Y. Wy,Org. Lett., 2000, 2, 891. D. L. Wright, L. C. Usher, and M. Estralla-Jimenez, Org. Lett., 2001, 3, 4275. D. A. Evans, P. H. Carter, E. M. Carreira, A. B. Charette, J. A. Prunet, and M. Lautens, J. Am. Chem. Soc., 1999, 121, 7540. D. A. Evans, D. M. Fitch, T. E. Smith, and B. J. Cee, J. Am. Chem. Soc., 2000, 122, 10033. T. P. Loh, J. Y. Yang, L. C. Feng, and Y. Zhou, Tetrahedron Lett., 2002, 43, 7193.
22. For representative examples of tetrahydropyranones in total synthesis see: L.-S. Li, Y.-L. Wu, and Y. Wy,Org. Lett., 2000, 2, 891. D. L. Wright, L. C. Usher, and M. Estralla-Jimenez, Org. Lett., 2001, 3, 4275. D. A. Evans, P. H. Carter, E. M. Carreira, A. B. Charette, J. A. Prunet, and M. Lautens, J. Am. Chem. Soc., 1999, 121, 7540. D. A. Evans, D. M. Fitch, T. E. Smith, and B. J. Cee, J. Am. Chem. Soc., 2000, 122, 10033. T. P. Loh, J. Y. Yang, L. C. Feng, and Y. Zhou, Tetrahedron Lett., 2002, 43, 7193.
23. For representative examples of tetrahydropyranones in total synthesis see: L.-S. Li, Y.-L. Wu, and Y. Wy,Org. Lett., 2000, 2, 891. D. L. Wright, L. C. Usher, and M. Estralla-Jimenez, Org. Lett., 2001, 3, 4275. D. A. Evans, P. H. Carter, E. M. Carreira, A. B. Charette, J. A. Prunet, and M. Lautens, J. Am. Chem. Soc., 1999, 121, 7540. D. A. Evans, D. M. Fitch, T. E. Smith, and B. J. Cee, J. Am. Chem. Soc., 2000, 122, 10033. T. P. Loh, J. Y. Yang, L. C. Feng, and Y. Zhou, Tetrahedron Lett., 2002, 43, 7193.
24. For representative examples of tetrahydropyranones in total synthesis see: L.-S. Li, Y.-L. Wu, and Y. Wy,Org. Lett., 2000, 2, 891. D. L. Wright, L. C. Usher, and M. Estralla-Jimenez, Org. Lett., 2001, 3, 4275. D. A. Evans, P. H. Carter, E. M. Carreira, A. B. Charette, J. A. Prunet, and M. Lautens, J. Am. Chem. Soc., 1999, 121, 7540. D. A. Evans, D. M. Fitch, T. E. Smith, and B. J. Cee, J. Am. Chem. Soc., 2000, 122, 10033. T. P. Loh, J. Y. Yang, L. C. Feng, and Y. Zhou, Tetrahedron Lett., 2002, 43, 7193.
25. J. D. Rainier, J. M. Cox, and S. P. Allwein, Tetrahedron Lett., 2001, 42, 179.
26. L. Alcarez, J. J. Harnett, C. Mioskowski, J. P. Martel, T. Le Gall, D.-S. Shin, and J. R. Falck, Tetrahedron Lett., 1994, 35, 5449.
27. Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, and K. B. Sharpless, J. Am. Chem. Soc., 1987, 109, 5765.
28. 2, 99%; 2) t-BuOK, THF, -15 °C, 80%; 3) NaI, acetone.
29. M. T. Crimmins, K. A. Emmitte, and J. D. Katz, Org. Lett., 2000, 2, 2165.
30. J. P. Morgan and R. H. Grubbs, Org. Lett., 2000, 2, 3153.