Carbonylative radical cyclization approaches to tri- and tetraquinanes: Sequential formation of three, four and five carbon-carbon bonds

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 10, 1998, Pages 1591-1593

  Curran, Dennis P ^a   Sisko, Joseph ^a   Balog, Aaron ^a   Sonoda, Noboru ^b   Nagahara, Kiyoto ^b   Ryu, Ilhyong ^b  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748517017     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a800352a     Document Type: Article

References (27)

1. (a) T. Anke, J. Heim, F. Knoch, U. Mocek, B. Steffan and W. Steglich, Angew. Chem., Int. Ed. Engl., 1985, 97, 709;
2. (b) J. Kupka, T. Anke, F. Oberwinkler, G. Schramm and W. Steglich, J. Antibiot., 1979, 32, 130.
3. (a) E. Piers and J. Renaud, J. Org. Chem., 1993, 58, 11. Other model studies:
4. (b) G. Mehta, K. S. Rao and M. S. Reddy, J. Chem. Soc., Perkin Trans. 1, 1991, 693;
5. (c) L. V. Tinao-Wooldridge, K. D. Moeller and C. M. Hudson, J. Org. Chem., 1994, 59, 2381;
6. (d) D. A. Frey, J. A. Marx and K. D. Moeller, Electrochim. Acta, 1997, 42, 1957;
7. (e) A. L. Veretenov, W. A. Smit, L. G. Vorontsova, M. G. Kurella, R. Caple and A. S. Gybin, Tetrahedron Lett., 1991, 32, 2109.
8. (a) D. P. Curran, Synlett, 1991, 63;
9. (b) D. P. Curran, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 4, p. 779.
10. Computer analysis of only the approaches with vicinal bond forming reactions reveals >100 possibilities. G. Mehta, R. Barone, P. Azario, F. Barberis, M. Arbelot and M. Chanon, Tetrahedron, 1992, 48, 8953.
11. (a) C. E. Schwartz and D. P. Curran, J. Am. Chem. Soc., 1990, 112, 9272;
12. (b) D. P. Curran, J. Sisko, P. E. Yeske and H. Liu, Pure Appl. Chem., 1993, 65, 1153;
13. (c) D. P. Curran and S. Sun, Aust. J. Chem., 1995, 48, 261.
14. I. Ryu, N. Sonoda and D. P. Curran, Chem. Rev., 1996, 96, 177.
15. T. J. Jenkins and D. J. Burnell, J. Org. Chem., 1994, 59, 1485.
16. A. Balog, S. J. Geib and D. P. Curran, J. Org. Chem, 1995, 60, 345.
17. Full details of the synthesis and characterization of all precursors as well as the X-ray structure can be found in the PhD Thesis of A. Balog, University of Pittsburgh, 1996.
18. I. Ryu and N. Sonoda, Angew. Chem., Int. Ed. Engl., 1996, 35, 1050.
19. For a review of stereoselection in radical cyclizations, see D. P. Curran, N. A. Porter and B. Giese, in Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications, VCH, Weinheim, 1996, ch. 2, p. 283.
20. For example, see: (a) D. P. Curran, E. Eichenberger, M. Collis, M. G. Roepel and G. Thoma, J. Am. Chem. Soc., 1994, 116, 4279;
21. (b) M. Newcomb, J. H. Horner and C. J. Emanuel, J. Am. Chem. Soc., 1997, 119, 7147;
22. (c) I. Ryu, H. Muraoka, N. Kambe, M. Komatsu and N. Sonoda, J. Org. Chem., 1996, 61, 6396.
23. (a) B. P. Branchaud, A. G. Glenn and H. C. Stiasny, J. Org. Chem., 1991, 56, 6656;
24. (b) B. P. Branchaud, M. P. Montague-Smith, D. J. Kosman and F. R. McLaren, J. Am. Chem. Soc., 1993, 115, 798.
25. (a) C. J. Hayes and G. Pattenden, Tetrahedron Lett., 1996, 37, 271;
26. (b) See also, I. Ryu, T. Okuda, K. Nagahara, N. Kambe, M. Komatsu and N. Sonoda, J. Org. Chem., 1997, 62, 7550.
27. B. B. Snider, Chem. Rev., 1996, 96, 339.