Chemoselective reductive cross-coupling of 1,5-diene-3-ols with alkynes: A facile entry to stereodefined skipped trienes

Journal of the American Chemical Society

Volumn 132, Issue 28, 2010, Pages 9576-9578

  Diez, Peter S ^a   Micalizio, Glenn C ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMOSELECTIVE; COMPLEX FRAGMENTS; CONVERGENT SYNTHESIS; CROSS-COUPLINGS; FUNCTIONALIZATIONS; SITE SELECTIVITY;

ACETYLENE; SYNTHESIS (CHEMICAL);

OLEFINS;

1,5 DIENE 3 OL; ALKADIENE; ALKYNE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; STEREOCHEMISTRY; SYNTHESIS;

ALKYNES; STEREOISOMERISM;

EID: 77954654941     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103836h     Document Type: Article

References (28)

1. Krey, G., Braissant, O., LHorset, F., Kalkhoven, E., Perroud, M., Parker, M. G., and Wahli, W. Mol. Endocrinol. 1997, 11, 779
2. Ringbom, T., Huss, U., Stenholm, Å, Flock, S., Skattebøl, L., Perera, P., and Bohlin, L. J. Nat. Prod. 2001, 64, 745
3. Hamilton, J. A. Prostag. Leukotr. Ess. 2006, 67, 65
4. Yaqoob, P. Trends Immunol. 2003, 24, 639
5. Lie Ken Jie, M. S. F., Pasha, M. K., and Syed-Rahmatullah, M. S. K. Nat. Prod. Rep. 1997, 14, 163
6. Irschik, H., Augustiniak, H., Gerth, K., Höefle, G., and Reichenback, H. J. Antibiot. 1995, 48, 787
7. Gerth, K., Washausen, P., Höefle, G., Irschik, H., and Reichenback, H. J. Antibiot. 1996, 49, 71
8. For a review of methods for the synthesis of (Z, Z)-1,4-dienes, see
9. Durand, S., Parrain, J.-L., and Santelli, M. J. Chem. Soc., Perkin Trans. 1 2000, 253
10. For carbonyl olefination-based methods to access skipped alkenes, see: Fürstner, A., Larionov, O., and Flügge, S. Angew. Chem., Int. Ed. 2007, 46, 5545
11. For recent reviews, see: Aïssa, C. Eur. J. Org. Chem. 2009, 1831
12. Demeunier, R. and Marko, I. E. In Modern Carbonyl Olefination; Takeda, T., Ed.; Wiley-VCH: Weinheim, 2004, p 104
13. For a route to 1,4-dienes by 1,5-hydrogen migrations in cis -vinylcyclopropanes, see: Ellis, R. J. and Frey, H. M. P. Chem. Soc. London 1964, 221
14. Parziale, P. A. and Berson, J. A. J. Am. Chem. Soc. 1990, 112, 1650
15. Parziale, P. A. and Berson, J. A. J. Am. Chem. Soc. 1991, 113, 4595
16. Macklin, T. K. and Micalizio, G. C. Nature Chem. 2010, 2, doi:10.1038/nchem.665.
17. Kolundzic, F. and Micalizio, G. C. J. Am. Chem. Soc. 2007, 129, 15112
18. See also
19. Lysenko, I. L., Kim, K., Lee, H. G., and Cha, J. K. J. Am. Chem. Soc. 2008, 130, 15997
20. Reichard, H. A. and Micalizio, G. C. Angew. Chem., Int. Ed. 2007, 46, 1440
21. 4, see
22. Kulinkovich, O. G. and Meijere, A. Chem. Rev. 2000, 100, 2789
23. Sato, F., Urabe, H., and Okamoto, S. Chem. Rev. 2000, 100, 2835
24. Regioselection in reductive cross-coupling is often challenging to control. For a recent review, see
25. Reichard, H. A., McLaughlin, M., Chen, M. Z., and Micalizio, G. C. Eur. J. Org. Chem. 2010, 391
26. For a recent example of ligand-controlled regioselective reductive cross-coupling of internal alkynes with aldehydes, see: Malik, H. A., Sormunen, G. J., and Montgomery, J. J. Am. Chem. Soc. 2010, 132, 6304
27. In Ni-catalyzed reductive cross-coupling of enynes with aldehydes, Jamison has demonstrated that the pendent alkene plays a role in regioselective functionalization of the alkyne; see: Miller, K. M. and Jamison, T. F. J. Am. Chem. Soc. 2004, 126, 15342
28. The method described herein does not rely on similar alkene direction and is tolerant of diverse alkene substitution and stereochemistry.