An approach to the synthesis of dimeric resveratrol natural products via a palladium-catalyzed domino reaction

Tetrahedron Letters

Volumn 50, Issue 17, 2009, Pages 1969-1972

  Jeffrey, Jenna L ^a   Sarpong, Richmond ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFULVENE; BROMOSTILBENE DERIVATIVE; CARBON; LEWIS ACID; PALLADIUM; RESVERATROL; STILBENE DERIVATIVE; TOLANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; DIMERIZATION; HECK REACTION; OXIDATION; SYNTHESIS;

EID: 61749095502     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.067     Document Type: Article

References (34)

1. For a review of domino reactions in organic synthesis, see:. Tietze L.F. Chem. Rev. 96 (1996) 115-136
2. For a review of the Heck reaction in modern synthesis and a list of several examples of palladium-catalyzed cascade reactions, see:. De Meijere A., and Meyer F.E. Angew. Chem., Int. Ed. Engl. 33 (1994) 2379-2411
3. Takaoka M. Proc. Imp. Acad. Tokyo 16 (1940) 405-407
4. Langcake P., and Pryce R.J. Physiol. Plant Pathol. 9 (1976) 77-86
5. Jang M., Cai L., Udeani G.O., Slowing K.V., Thomas C.F., Beecher C.W.W., Fong H.H.S., Farnsworth N.R., Kinghorn A.D., Mehta R.G., Moon R.C., and Pezzuto J.M. Science 275 (1997) 218-220
6. Valenzano D.R., Terzibasi E., Genade T., Cattaneo A., Domenici L., and Cellerino A. Curr. Biol. 16 (2006) 296-300
7. Ohyama M., Tanaka T., and Iinuma M. Phytochemistry 38 (1995) 733-740
8. Ohyama M., Tanaka T., and Iinuma M. Chem. Pharm. Bull. 42 (1994) 2117-2120
9. Adesanya S.A., Nia R., Martin T.M., Boukamcha N., Montagnac A., and Pais M. J. Nat. Prod. 62 (1999) 1694-1695
10. Luo H.-F., Zhang L.-P., and Hu C.-Q. Tetrahedron 57 (2001) 4849-4854
11. Li W.W., Ding L.S., Li B.G., and Chien Y.Z. Phytochemistry 42 (1996) 1163-1165
12. Tanaka T., Ito T., Nakaya K., Iinuma M., and Riswan S. Phytochemistry 54 (2000) 63-69
13. Coggon P., Janes N.F., King T.J., and Wallwork S.C. J. Chem. Soc. (1965) 406-408
14. Ito T., Tanaka T., Iinuma M., Iliya I., Nakaya K., Ali Z., Takahashi Y., Sawa R., Shirataki Y., Murata J., and Darnaedi D. Tetrahedron 59 (2003) 5347-5363
15. Supudompol B., Likhitwitayawuid K., and Houghton P.J. Phytochemistry 65 (2004) 2589-2594
16. Sahadin, Hakim E.H., Juliawaty L.D., Syah Y.M., bin Din L., Ghisalberti E.L., Latip J., Said I.M., and Achmad S.A.Z. Naturforsch., C: Biosci. 60 (2005) 723-727
17. Ito T., Tanaka T., Iinuma M., Nakaya K., Takahashi Y., Sawa R., Murata J., and Darnaedi D. J. Nat. Prod. 67 (2004) 932-937
18. Snyder S.A., Zografos A.L., and Lin Y. Angew. Chem., Int. Ed. 46 (2007) 8186-8191
19. Snyder, S. A.; Breazzano, S. P.; Ross, A. G.; Lin, Y.; Zografos, A. L. J. Am. Chem. Soc. 2009. doi: 10.1021/ja806183r.
20. Li W., Li H., Li Y., and Hou Z. Angew. Chem., Int. Ed. 45 (2006) 7609-7611
21. Anstead G.M., Ensign J.L., Peterson C.S., and Katzenellenbogen J.A. J. Org. Chem. 54 (1989) 1485-1491
22. Nazarov I.N., and Zaretskaya I.I. Bull. Acad. Sci. U.R.S.S., Classe sci. chim. (1942) 200-209
23. For a review of the Nazarov cyclization, see:. Habermas K.L., Denmark S.E., and Jones T.K. Org. React. 45 (1994) 1-158
24. Brand K., and Krey W. J. Prakt. Chem. 110 (1925) 10-25
25. +: 269.1172].
26. Ramirez F., Desai N.B., and McKelvie N. J. Am. Chem. Soc. 84 (1962) 1745-1747
27. Corey E.J., and Fuchs P.L. Tetrahedron Lett. 13 (1972) 3769-3772
28. For a review of alkyne synthesis using phosphorous compounds, see:. Eymery F., Iorga B., and Savignac P. Synthesis (2000) 185-213
29. Nakamura H., Kuroda H., Saito H., Suzuki R., Yamori T., Maruyama K., and Haga T. Chem. Med. Chem. 1 (2006) 729-740
30. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. (1975) 4467-4470
31. For a review of organopalladium chemistry in organic synthesis, see:. Sonogashira K. Synthesis 1 (2002) 493-529
32. +: 536.2199]; mp 158-159 °C.
33. +: 534.2042]; mp 242-243 °C.
34. Kovacic P., and Jones M.B. Chem. Rev. 87 (1987) 357-379