Synthesis of a tricyclic core of rameswaralide

Tetrahedron Letters

Volumn 51, Issue 48, 2010, Pages 6232-6235

  Trost, Barry M ^a   Nguyen, Hien M ^b   Koradin, Christopher ^a  

^a STANFORD UNIVERSITY   (United States)

^b E11 SSH   (United States)

Author keywords

Cycloaddition; Reductive radical cyclization; Ruthenium; The fused bicyclic system; Total synthesis

Indexed keywords

DIHYDRORAMESWARALIDE; DITERPENE; RAMESWARALIDE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL MODIFICATION; CYCLOADDITION; DEHYDROSULFENYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY;

EID: 78049401890     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.042     Document Type: Article

References (39)

1. P. Ramesh, N.S. Reddy, Y. Venkateswarlu, M.V.R. Reddy, and J.D. Faulkner Tetrahedron Lett. 39 1998 8217 8220
2. Faulkner, J. D.; Venkateswarlue, Y. PCT Int. Appl. WO 00,27,839, 2000.
3. A. Srikrishna, and D.H. Dethe Org. Lett. 6 2004 165 168
4. G. Mehta, and S. Lakshminath Tetrahedron Lett. 47 2006 327 330
5. G. Pattenden, and J.M. Winne Tetrahedron Lett. 50 2009 7310 7313
6. R.N. Saici, and S.Z. Zard Chem. Commun. 1996 1631 1632
7. S.Z. Zard Angew. Chem., Int. Ed. 36 1997 672 685
8. J.F. Forbes, R.N. Saicic, and S.Z. Zard Tetrahedron 55 1999 3791 3802
9. B.M. Trost, F.D. Toste, and H. Shen J. Am. Chem. Soc. 122 2000 2379 2380
10. B.M. Trost, and H. Shen Angew. Chem., Int. Ed. 40 2001 2313 2316
11. B.M. Trost, H.C. Shen, T. Schulz, C. Koradin, and H. Schirok Org. Lett. 5 2003 4149 4151
12. B.M. Trost, H.C. Shen, D.B. Horne, F.D. Toste, B.G. Steinmetz, and C. Koradin Chem. Eur. J. 11 2005 2577 2590
13. B.M. Trost, Y. Hu, and D.B. Horne J. Am. Chem. Soc. 129 2007 11781 11790
14. B.M. Trost, J. Waser, and A. Meyer J. Am. Chem. Soc. 129 2007 11970 11978
15. For rhodium-catalyzed [5+2]-cycloaddition, see the following representative articles: P. Liu, L.E. Sirois, P.H.-Y. Cheong, Z.-H. Yu, I.V. Hartung, H. Rieck, and P.A. Wender J. Am. Chem. Soc. 132 2010 10127 10135
16. P.A. Wender, R.T. Stemmler, and L.E. Sirois J. Am. Chem. Soc. 132 2010 2532 2533
17. P. Liu, P.H.-Y. Cheong, Z.-X. Yu, P.A. Wender, and K.N. Houk Angew. Chem., Int. Ed. 47 2008 3939 3941
18. Z.-X. Yu, P.H.-Y. Cheong, P. Liu, C.Y. Legault, P.A. Wender, and K.N. Houk J. Am. Chem. Soc. 130 2008 2378 2379
19. P.A. Wender, L.O. Haustedt, J. Lim, J.A. Love, T.J. Williams, and J.-Y. Yoon J. Am. Chem. Soc. 128 2006 6302 6303
20. P.A. Wender, C.O. Husfeld, E. Langkopf, and J.A. Love J. Am. Chem. Soc. 120 1998 1940 1941
21. P.A. Wender, H. Takahashi, and B. Witulski J. Am. Chem. Soc. 117 1995 4720 4721
22. K.-M. Chen, K.G. Gunderson, G.E. Hardtmann, K. Prasad, O. Repic, and M.J. Shapiro Chem. Lett. 1987 1923 1926
23. K.-M. Chen, G.E. Hardtmann, K. Prasad, O. Repic, and M.J. Shapirio Tetrahedron Lett. 28 1987 155 158
24. D.A. Evans, and A.H. Hoveyda J. Org. Chem. 55 1990 5190 5192
25. S.D. Rychnovsky, B. Rogers, and G. Yang J. Org. Chem. 58 1993 3511 3515
26. G. Stork, and M. Kahn J. Am. Chem. Soc. 107 1985 500 501
27. G. Stork, and P.M. Sher J. Am. Chem. Soc. 108 1986 303 304
28. D.P. Curran, M.-H. Chen, and D. Kim J. Am. Chem. Soc. 111 1989 626506276
29. D.P. Curran, and J. Tamine J. Org. Chem. 56 1991 2746 2750
30. V.H. Rawal, S.P. Singh, S.C. Dufour, and C. Michoud J. Org. Chem. 56 1991 5245 5247
31. M. Bachi, and E. Bosch J. Org. Chem. 57 1992 4696 4705
32. D.L.J. Clive, H.W. Manning, T.L.B. Boivin, and M.H.D. Posteman J. Org. Chem. 58 1993 6857 6873
33. D. Crich, C. Chen, J.-T. Hwang, H. Yuan, A. Papadatos, and R.I. Walter J. Am. Chem. Soc. 116 1994 8937 8951
34. M.A. Lucas, and C.H. Schiesser J. Org. Chem. 61 1996 5754 5761
35. A. Studer, and S. Amerein Synthesis 2002 835 849
36. H. Yorimitsu, H. Shinokubo, and K. Oshima Synlett 2002 674 686
37. J. Tsuji, I. Minami, and I. Shimizu Tetrahedron Lett. 24 1983 5639 5640
38. B.M. Trost, T.N. Salzmann, and K. Hiroi J. Am. Chem. Soc. 98 1976 4887 4902
39. B.M. Trost, and G.S. Massiot J. Am. Chem. Soc. 99 1977 4405 4412