Reaction modes of oxidative dimerization of epoxycyclohexenols

Tetrahedron Letters

Volumn 44, Issue 38, 2003, Pages 7205-7207

  Shoji, Mitsuru ^a   Kishida, Satoshi ^a   Kodera, Yusuke ^a   Shiina, Isamu ^a   Kakeya, Hideaki ^b   Osada, Hiroyuki ^b   Hayashi, Yujiro ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b Discovery Research Institute   (Japan)

Author keywords

6 electrocylization; Diels Alder reaction; Epoxyquinol; Hydrogen bonding

Indexed keywords

2 ALKENYL 3 HYDROXYMETHYL 2 CYCLOHEXEN 1 ONE; EPOXIDE; EPOXYQUINONE; KETONE DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DESS MARTIN OXIDATION; DIELS ALDER REACTION; DIMERIZATION; HYDROGEN BOND; MOLECULAR INTERACTION; OXIDATION; STRUCTURE ANALYSIS;

BETULACEAE; HOMO;

EID: 0043011180     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01781-7     Document Type: Article

References (23)

1. Kakeya H., Onose R., Koshino H., Yoshida A., Kobayashi K., Kageyama S.-I., Osada H. J. Am. Chem. Soc. 124:2002;3496.
2. Kakeya H., Onose R., Yoshida A., Koshino H., Osada H. J. Antibiot. 55:2002;829.
3. Shoji M., Yamaguchi J., Kakeya H., Osada H., Hayashi Y. Angew. Chem., Int. Ed. 41:2002;3192.
4. Hayashi Y., Nakamura M., Nakao S., Inoue T., Shoji M. Angew. Chem., Int. Ed. 41:2002;4079.
5. Shoji M., Kishida S., Takeda M., Kakeya H., Osada H., Hayashi Y. Tetrahedron Lett. 43:2002;9155.
6. Li C., Bardhan S., Pace E.A., Liang M.-C., Gilmore T.D., Porco J.A. Jr. Org. Lett. 4:2002;3267.
7. Mehta G., Islam K. Tetrahedron Lett. 44:2003;3569.
8. 3.
9. The 16 possible reaction modes are as follows: endo-anti(epoxide)-anti(Me)-hetero, exo-anti(epoxide)-anti(Me)-homo, endo-anti(epoxide)-anti(Me)-homo, exo-anti(epoxide)-anti(Me)-hetero, endo-anti(epoxide)-syn(Me)-hetero, exo-anti(epoxide)-syn(Me)-homo, endo-anti(epoxide)-syn(Me)-homo, exo-anti(epoxide)-syn(Me)-hetero, endo-syn(epoxide)-anti(Me)-hetero, exo-syn(epoxide)-anti(Me)-homo, endo-syn(epoxide)-anti(Me)-homo, exo-syn(epoxide)-anti(Me)-hetero, endo-syn(epoxide)-syn(Me)-hetero, exo-syn(epoxide)-syn(Me)-homo, endo-syn(epoxide)-syn(Me)-homo, exo-syn(epoxide)-syn(Me)-hetero.
10. Dess D.B., Martin J.C. J. Org. Chem. 48:1983;4115.
11. Dess D.B., Martin J.C. J. Am. Chem. Soc. 113:1991;7277.
12. Ireland R.E., Liu L. J. Org. Chem. 58:1993;2899.
13. Syntheses of 6, 9 and 11 will be published in a full account.
14. Li C., Lobkovsky E., Porco J.A. Jr. J. Am. Chem. Soc. 122:2000;10484.
15. Li C., Johnson R.P., Porco J.A. Jr. J. Am. Chem. Soc. 125:2003;5095.
16. Hu Y., Li C., Kulkarni B.A., Strobel G., Lobkovsky E., Torczynski R.M., Porco J.A. Jr. Org. Lett. 3:2001;1649.
17. Because of the lack of epoxide in 9, the number of possible reaction modes is reduced from sixteen in 3 to eight.
18. References using inter-molecular hydrogen-bonding for the control of stereochemistry of Diels-Alder reaction, see: (a) Atherton, C. J. C.; Jones, S. Tetrahedron Lett. 2001, 42, 8239; (b) Tripathy, R.; Carroll, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1990, 112, 6743; (c) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625.
19. References using inter-molecular hydrogen-bonding for the control of stereochemistry of Diels-Alder reaction, see: (a) Atherton, C. J. C.; Jones, S. Tetrahedron Lett. 2001, 42, 8239; (b) Tripathy, R.; Carroll, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1990, 112, 6743; (c) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625.
20. References using inter-molecular hydrogen-bonding for the control of stereochemistry of Diels-Alder reaction, see: (a) Atherton, C. J. C.; Jones, S. Tetrahedron Lett. 2001, 42, 8239; (b) Tripathy, R.; Carroll, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1990, 112, 6743; (c) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625.
21. Grieco P.A., Nunes J.J., Gaul M.D. J. Am. Chem. Soc. 112:1990;4595.
22. Gillard J.R., Newlands M.J., Bridson J.N., Burnell D.J. Can. J. Chem. 69:1991;1337.
23. Fleming I. Frontier Orbitals and Organic Chemical Reactions. 1976;John Wiley & Sons, Chichester, UK.