Tetraquinanes via [4 + 4] photocycloaddition/transannular ring closure

Organic Letters

Volumn 12, Issue 20, 2010, Pages 4510-4512

  Chen, Peiling ^a   Carroll, Patrick J ^b   Sieburth, Scott McN ^a  

^a Temple University   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77957848391     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101802s     Document Type: Article

References (36)

1. Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-719
2. Singh, V.; Thomas, B. Tetrahedron 1998, 54, 3647-3692
3. Anke, T.; Heim, J.; Knoch, F.; Mocek, U.; Steffan, B.; Steglich, W. Angew. Chem., Int. Ed. 1985, 24, 709-711
4. Kupka, J.; Anke, T.; Oberwinkler, F.; Schramm, G.; Steglich, W. J. Antibiot. 1979, 32, 130-135
5. Shinohara, C.; Chikanishi, T.; Nakashima, S.; Hashimoto, A.; Hamanaka, A.; Endo, A.; Hasumi, K. J. Antibiot. 2000, 53, 262-268
6. Mehta, G.; Rao, K. S. Chem. Commun. 1987, 157, 8-80
7. Mehta, G.; Rao, K. S.; Reddy, M. S. Tetrahedron Lett. 1988, 29, 5025-8
8. Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272-84
9. Griesbeck, A. G. Chem. Ber. 1990, 123, 549-554
10. Mehta, G.; Rao, K. S.; Reddy, M. S. J. Chem. Soc., Perkin Trans. 1991, 1, 693-700
11. Zhang, C.; Wu, S. F.; Guo, X. C. Chin. Chem. Lett. 1994, 5, 561-562
12. Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1998, 1, 1591-1593
13. Piers, E.; Renaud, J.; Rettig, S. J. Synthesis 1998, 590-602
14. Wender, P. A.; Dore, T. M. Tetrahedron Lett. 1998, 39, 8589-8592
15. Transannular ring closure of cyclooctanoids to diquinanes can be be effected in many ways. For lead references see
16. Ader, T. A.; Champey, C. A.; Kuznetsova, L. V.; Li, T.; Lim, Y.-H.; Rucando, D.; Sieburth, S. McN. Org. Lett. 2001, 3, 2165-2167
17. For a related, elegant approach to polyquinanes based on [4 + 4] photocycloaddition of a 2-pyrone with a furan, see
18. Li, L.; McDonald, R.; West, F. G. Org. Lett. 2008, 10, 3733-3736
19. Sieburth, S. McN.; McGee, K. F., Jr.; Zhang, F.; Chen, Y. J. Org. Chem. 2000, 65, 1972-1977
20. Sieburth, S. McN. in CRC Handbook of Organic Photochemistry and Photobiology, (Eds: Horspool, W.; Lenci, F.), CRC Press, Boca Raton, FL, 2004, pp 103/1 - 103/18.
21. Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J.-l. J. Am. Chem. Soc. 1996, 118, 10803-10810
22. Sieburth, S. McN.; Lin, C.-H. J. Org. Chem. 1994, 59, 3597-3599
23. Sieburth, S. McN.; McGee, K. F., Jr.; Al-Tel, T. H. J. Am. Chem. Soc. 1998, 120, 587-588
24. Lim, Y.-H.; Li, T.; Chen, P.; Schreiber, P.; Kutnetsova, L.; Carroll, P. J.; Lauher, J. W.; Sieburth, S. McN. Org. Lett. 2005, 7, 5413-5415 See also reference (6)
25. Initial studies Chen, P.; Chen, Y.; Carroll, P. J.; Sieburth, S. McN. Org. Lett. 2006, 8, 3367-3370
26. In a closely related study of the effect of stereochemistry on 2-pyrone-furan [4 + 4]-photocycloaddition, with the opposite steric effect, see
27. Song, D.; McDonald, R.; West, F. G. Org. Lett. 2006, 8, 4075-4078
28. For a recent discussion of cis-trans.stereoselectivity in 2-pyrone-furan [4 + 4]-photocycloadditions, see
29. Li, L.; Chase, C. E.; West, F. G. Chem. Commun. 2008, 4025-4027
30. Li, L.; Bender, J. A.; West, F. G. Tetrahedron Lett. 2009, 50, 1188-1192
31. 2=0.0843. See Supporting Information.
32. A reviewer has made the very reasonable suggestion that the formation of 23 could also be explained by addition of a radical bromination process.
33. Brown, C. A. J. Org. Chem. 1974, 39, 1324-1325
34. Brown, C. A. J. Org. Chem. 1974, 39, 3913-3918
35. Hudrlik, P. F.; Takacs, J. M. J. Org. Chem. 1978, 43, 3861-3865
36. 2=0.0850. See Supporting Information.