Catalyst-controlled formal [4 + 3] cycloaddition applied to the total synthesis of (+)-barekoxide and (-)-Barekol

Journal of the American Chemical Society

Volumn 132, Issue 35, 2010, Pages 12422-12425

  Lian, Yajing ^a   Miller, Laura C ^b   Born, Stephen ^b   Sarpong, Richmond ^b   Davies, Huw M L ^a  

^a EMORY UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPE REARRANGEMENT; CYCLOADDITIONS; CYCLOPROPANATION; DIRHODIUM; TOTAL SYNTHESIS;

CATALYSTS; CYCLOADDITION; OLEFINS; RHODIUM;

SYNTHESIS (CHEMICAL);

ACETIC ACID DERIVATIVE; ALKADIENE; BAREKOL; BAREKOXIDE; CYCLOPROPANE DERIVATIVE; OXIDE; RHODIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; COPE REARRANGEMENT; CYCLOADDITION; CYCLOPROPANATION; ENANTIOSELECTIVITY; SYNTHESIS;

CATALYSIS; CYCLIZATION; DITERPENES; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; RHODIUM; STEREOISOMERISM;

EID: 77956246696     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103916t     Document Type: Article

References (22)

1. For recent reviews, see
2. Maimone, T. J. and Baran, P. S. Nat. Chem. Biol. 2007, 3, 396
3. Salem, M. M. and Werbovetz, K. A. Curr. Med. Chem. 2006, 13, 2571
4. Sosa, M. E. and Tonn, C. E. Phytochem Rev. 2008, 7, 3
5. For reviews, see
6. Davies, H. M. L. and Denton, J. R. Chem. Soc. Rev. 2009, 38, 3061
7. Davies, H. M. L. In Advances in Cycloadditions; Harmata, M., Ed.; JAI Press: Greenwich, CT, 1998; Vol. 5, pp 119 - 164.
8. For recent examples, see
9. Olson, J. P. and Davies, H. M. L. Org. Lett. 2008, 10, 573
10. Reddy, R. P. and Davies, H. M. L. J. Am. Chem. Soc. 2007, 129, 10312
11. Schwartz, B. D., Denton, J. R., Lian, Y., Davies, H. M. L., and Williams, C. M. J. Am. Chem. Soc. 2009, 131, 8329
12. Davies, H. M. L., Stafford, D. G., Doan, B. D., and Houser, J. H. J. Am. Chem. Soc. 1998, 120, 3326
13. Miller, L. C., Ndungu, J. M., and Sarpong, R. Angew. Chem., Int. Ed. 2009, 48, 2398
14. Justicia, J., Oller-Loěpez, J. L., Campaña, A. G., Oltra, J. E., Cuerva, J. M., Buñuel, E., and Caěrdenas, D. J. J. Am. Chem. Soc. 2005, 127, 14911
15. Rudi, A., Shalom, H., Schleyer, M., Benayahu, Y., and Kashman, Y. J. Nat. Prod. 2004, 67, 106
16. Kuniyoshi, M., Marma, M. S., Higa, T., Bernardinelli, G., and Jefford, C. W. Chem. Commun. 2000, 1155
17. Rudi, A. and Kashman, Y. J. Nat. Prod. 1992, 55, 1408
18. 4: Tetrakis[(S)-(-)- N -(p -dodecylphenylsulfonyl)prolinato]-dirhodium (CAS 179162-34-6).
19. 4: Tetrakis[(S)-(+)-(1-adamantyl)-(N -phthalimido)acetato]-dirhodium(II) (CAS 909393-65-3).
20. Hansen, J., Autsbach, J., and Davies, H. M. L. J. Org. Chem. 2009, 74, 6555
21. Gevorgyan, V., Rubin, M., Benson, S., Liu, J., and Yamamoto, Y. J. Org. Chem. 2000, 65, 6179
22. The crystal structure of (-)-barekol (2) has been deposited at the Cambridge Crystallographic Data Centre, and the deposition number CCDC-776944 has been allocated. It adopts two conformations in the crystal, which supports the structure analysis by Kashman (6b)