Total syntheses of (±)-frondosin C and (±)-8-epi-frondosin C via a tandem anionic 5-exo dig cyclization-Claisen rearrangement sequence

Tetrahedron

Volumn 63, Issue 9, 2007, Pages 1899-1906

  Li, Xin ^a   Kyne, Robert E ^a   Ovaska, Timo V ^a  

^a The Holleran Center for Community Action and Public Policy   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

11 (TERT BUTYLDIMETHYLSILYLOXY) 4,4,7 TRIMETHYL 1,2,3,4,4A,5,7A,8 OCTAHYDRODIBENZO[A,H]AZULEN 6(2H) ONE; 11 (TERT BUTYLDIMETHYLSILYLOXY) 4,4,7 TRIMETHYL 1,2,3,4,5,6,7,8 OCTAHYDRODIBENZO[A,H]AZULEN 6 OL; 11 (TERT BUTYLDIMETHYLSILYLOXY) 4,4,7 TRIMETHYL 1,2,3,4,5,6,7,8 OCTAHYDRODIBENZO[A,H]AZULENE; 11 (TERT BUTYLDIMETHYLSILYLOXY) 4,4,7 TRIMETHYL 1,2,3,4,5,8 HEXAHYDRODIBENZO[A,H]AZULEN 6(2H) ONE; 4,4,7 TRIMETHYL 1,2,3,4,5,6,7,8 OCTAHYDRODIBENZO[A,H]AZULEN 11 OL; 6 (TERT BUTYLDIMETHYLSILYLOXY) 1 (3,3 DIMETHYLCYCLOHEX 1 ENYL) 2 (1 METHYL 3 TRIMETHYLSILYLPROP 2 YN 1 YL)INDAN OL; 6 (TERT BUTYLDIMETHYLSILYLOXY) 1 (3,3 DIMETHYLCYCLOHEX 1 ENYL) 2 (1 METHYLPROP 2 YN 1 YL)INDAN 1 OL; 6 (TERT BUTYLDIMETHYLSILYLOXY) 2 (1 METHYL 3 TRIMETHYLSILYLPROP 2 YN 1 YL)INDAN 1 ONE; 6 HYDROXY 2 [1 METHYL 3 (TRIMETHYLSILYL)PROP 2 YN 1 YL]INDAN 1 ONE; 6 HYDROXYINDAN 1 ONE DIMETHYLHYDRAZONE; ANION; FRONDOSIN A; FRONDOSIN B; FRONDOSIN C; FRONDOSIN E; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CLAISEN REARRANGEMENT; CYCLIZATION; DRUG ACTIVITY; DRUG SYNTHESIS; IRRADIATION; ISOMERIZATION; MICROWAVE RADIATION; NONHUMAN; PRIORITY JOURNAL; PROTON TRANSPORT; STRUCTURE ACTIVITY RELATION;

EID: 33846384050     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.12.057     Document Type: Article

References (41)

1. Marvell E.N., and Titterington D. Tetrahedron Lett. (1980) 2123
2. Ovaska T.V., Roark J.L., and Shoemaker C.M. Tetrahedron Lett. 39 (1998) 5705
3. Ovaska T.V., and Roses J.B. Org. Lett. 2 (2000) 2361
4. Ovaska T.V., Reisman S.E., and Flynn M.A. Org. Lett. 3 (2001) 115
5. Ovaska T.V., Ravi Kumar J.S., Hulford C.A., O'Sullivan M.F., and Reisman S.E. Tetrahedron Lett. 43 (2002) 1939
6. McIntosh C.E., Martinez I., and Ovaska T.V. Synlett (2004) 2579
7. Martinez I., Alford P.E., and Ovaska T.V. Org. Lett. 7 (2005) 1133
8. Li X., Kyne R.E., and Ovaska T.V. Org. Lett. 8 (2006) 5153
9. Paquette L.A., Friedrich D., and Rogers R.D. J. Org. Chem. 56 (1991) 3841
10. Rhoads S.J., and Watson J.M. J. Am. Chem. Soc. 93 (1971) 5813
11. Fuhry M.A.M., Holmes A.B., and Marshall D.R. J. Chem. Soc., Perkin Trans. 1 (1993) 2743
12. For a recent review on transition metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes, see:. Alonso F., Beletskaya I.P., and Yus M. Chem. Rev. 104 (2004) 3079
13. Paul R., and Tchelitcheff S. Bull. Soc. Chim. Fr. 808 (1952) 812
14. Eglington G., Jones E.R.H., and Whiting M.C. J. Chem. Soc. (1952) 2873
15. Hiroya K., Jouka R., Yasuhara A., and Sakamoto T. Tetrahedron 57 (2001) 9697
16. Rhoads S.J., and Brandenburg C.F. J. Am. Chem. Soc. 93 (1971) 5805
17. Brook A.G. Acc. Chem. Res. 7 (1974) 77
18. Patil A.D., Freyer A.J., Killmer L., Offen P., Carte B., Jurewicz A.J., and Johnson R.K. Tetrahedron 53 (1997) 5047
19. Seitz M., Dewald B., Gerber N., and Baggiolini M. J. Clin. Invest. 87 (1991) 463
20. Miller E.J., Cohen A.B., Nagao D., Griffith R.J., Maunder R.J., Martin T.R., Weiner-Kronish J.P., Sticherling M., Christophers E., and Matthay M.A. Am. Rev. Respir. Dis. 146 (1992) 247
21. Brat D.J., Bellail A.C., and Van Meir E.G. Neuro Oncol. 7 (2005) 122
22. Zhu Y.M., Webster S.J., Flower D., and Woll P.J. Br. J. Cancer 91 (2004) 1970
23. Yuan A., Chen J.J., Yao P.L., and Yang P.C. Front. Biosci. (2005) 853
24. Lane B.R., Liu J., Bock P.J., Schols D., Coffey M.J., Strieter R.M., Polverini P.J., and Markovitz D.M. J. Virol. 76 (2002) 11570
25. Lane B.R., Lore K., Bock P.J., Andersson J., Coffey M.J., Strieter R.M., and Markovitz D.M. J. Virol. 75 (2001) 8195
26. Danishefsky S.J., Inoue M., and Frontier A.J. Angew. Chem., Int. Ed. 39 (2000) 761
27. Inoue M., Carson M.W., Frontier A.J., and Danishefsky S.J. J. Am. Chem. Soc. 123 (2001) 1878
28. Hughes C.C., and Trauner D. Angew. Chem., Int. Ed. 41 (2002) 1569
29. Hughes C.C., and Trauner D. Tetrahedron 60 (2004) 9675
30. Kerr D.J., Willis A.C., and Flynn B.L. Org. Lett. 6 (2004) 457
31. Nayak M.K., and Chakraborti A.K. Tetrahedron Lett. 38 (1997) 8749
32. Gavande N.S., Kundu S., Badgujar N.S., Kaur G., and Chakraborti A.K. Tetrahedron 62 (2006) 4201
33. Jung M.E., and Lyste M.A. J. Org. Chem. 42 (1977) 3761
34. Pasto D.J., and Taylor R.T. Org. React. 40 (1991) 91
35. Murahashi S.-I., Naota T., Miyaguchi N., and Noda S. J. Am. Chem. Soc. 118 (1996) 2509
36. Herrero M.T., Moreno I., Tellitu I., Dominguez E., and SanMartin R. Trends Heterocycl. Chem. 9 (2003) 91
37. Kita Y., Tohma H., and Yakura T. Trends Org. Chem. 3 (1992) 113
38. McKillop A., McLaren L., and Taylor R.J.K. J. Chem. Soc., Perkin Trans. 1 (1994) 2047
39. Mal D., Roy H.N., Hazra N.K., and Adhikari S. Tetrahedron 53 (1997) 2177
40. Wipf P., and Kim Y. J. Am. Chem. Soc. 116 (1994) 11678
41. Watson S.C., and Eastham J.F. J. Organomet. Chem. 9 (1967) 165