Selective synthesis of (2Z,4E)-dienyl esters by ene-diene cross metathesis

Organic Letters

Volumn 9, Issue 1, 2007, Pages 5-8

  Moura Letts, Gustavo ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DICTYOSTATIN; ESTER; MACROLIDE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CATALYSIS; ESTERS; MACROLIDES; MOLECULAR STRUCTURE; SOLVENTS;

EID: 33846404505     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062017d     Document Type: Article

References (31)

1. (a) Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Boyd, M. R.; Schmidt, J. M. J. Chem. Soc., Chem. Commun. 1994, 1111-1112.
2. (b) Isbrucker, R. A.; Cummins, J.; Pomponi, S. A.; Longley, R. E.; Wright, A. E. Biochem. Pharm. 2003, 66, 75-82.
3. (c) Paterson, I.; Britton, R.; Delgado, O.; Wright, A. E. Chem. Commun. 2004, 632-633.
4. (a) Paterson, I.; Anderson, E. A. Science 2005, 310, 451-453.
5. (b) Gunasekera, S. P.; Wright, A. E. In Anticancer Agents from Natural Products; Cragg, G. M., Kingston, D. G. I., Newman, D. J., Eds.; CRC Taylor Francis: New York, NY, 2005; pp 171-189.
6. (a) Shin, Y.; Choy, N.; Turner, T. R.; Balachandran, R.; Madiraju, C.; Day, B. W.; Curran, D. P. Org. Lett. 2002, 4, 4443-4446.
7. (b) Paterson, I.; Britton, R.; Delgado, O.; Meyer, A.; Poullennec, K. G. Angew. Chem., Int. Ed. 2004, 43, 4629-4633.
8. (c) Shin, Y.; Fournier, J. H.; Fukui, Y.; Bruckner, A. M.; Curran, D. P. Angew. Chem., Int. Ed. 2004, 43, 4634-4637.
9. (d) Shin, Y.; Fournier, J. H.; Balachandran, R.; Madiraju, C.; Raccor, B. S.; Zhu, G.; Edler, M. C.; Hamel, E.; Day, B. W.; Curran, D. P. Org. Lett. 2005, 7, 2873-2876.
10. (e) O'Neil, G. W.; Phillips, A. J. J. Am. Chem. Soc. 2006, 128, 5340-5341.
11. (f) Fukui, Y.; Brückner, A. M.; Shin, Y.; Balachandran, R.; Day, B. W.; Curran, D. P. Org. Lett. 2006, 8, 301-304.
12. (g) Jagel, J.; Maier, M. E. Synlett 2006, 693-696.
13. (h) Shin, Y.; Fournier, J.-H.; Brückner, A.; Madiraju, C.; Edler, M. C.; Vogt, A.; Balachandran, R.; Raccor, B. S.; Zhu, G.; Hamel, E.; Day, B. W.; Curran, D. P. Manuscript in preparation.
14. (i) Jung, W.-H; Harrison, C.-H.; Shin, Y.; Fournier, J.-H.; Madiraju, C.; Edler, M. C.; Vogt, A.; Balachandran, R.; Raccor, B. S.; Zhu, G.; Hamel, E.; Day, B. W.; Curran, D. P. Manuscript in preparation.
15. (a) Grubbs, R. H.; Trnka, T. M. In Ruthenium in Organic Synthesis; Murahashi, S.-I., Ed.; Wiley-VCH: Weinheim, 2004; pp 153-178.
16. (b) Grubbs, R. H. Handbook of Metathesis; Wiley-VCH: Weinheim, 2003.
17. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
18. (d) Schuster, M.; Blechert, S. Angew. Chem. Int., Ed. Engl. 1997, 2037-2056.
19. (e) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317-1382.
20. Funk, T. W.; Efskind, J.; Grubbs, R. H. Org. Lett. 2005, 7, 187-190.
21. (a) Light fluorous metathesis catalysts with SPE separation: Matsugi, M.; Curran, D. P. J. Org. Chem. 2005, 70, 1636-1642.
22. (b) Heavy fluorous metathesis catalyst with liquid-liquid separation: Yao, Q. W.; Zhang, Y. L. J. Am. Chem. Soc. 2004, 126, 74-75.
23. (c) Heavy fluorous catalyst with fluorous silica support: Michalek, F.; Bannwarth, W. Helv. Chim. Acta. 2006, 89, 1030-1037.
24. (d) Catalyst with dissociatable fluorous phosphine: da Costa, R. C.; Gladysz, J. A. Chem. Commun. 2006, 2619-2621.
25. Fluorous reagents and FluoroFlash silica products were purchased from Fluorous Technologies, Inc. D.P.C. holds an equity interest in this company.
26. 1H NMR, TLC) was generated by self-metathesis of 9 in the absence of 7.
27. Brummond, K. M.; Mitasev, B. Org. Lett. 2004, 6, 2245-2248.
28. Reviews on fluorous SPE: (a) Curran, D. P. In The Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horvath, I. T., Eds.; Wiley-VCH: Weinheim, 2004; pp 101-127.
29. (b) Curran, D. P. Aldrichim. Acta 2006, 39, 3-9.
30. (c) Zhang, W.; Curran, D. P. Tetrahedron 2006, in press.
31. 1H NMR spectrum was generated by metathesis of 15 in the absence of 7.) The entire mixture fraction was directly reused in a cross metathesis with 7 to provide an additional 20% of pure 16 after fspe and flash chromatography. Including the reuse of the mixture fraction raises the overall yield of 16 based on 15 in cycle 1 to 79%.