Flavonoid epoxides. Part 20. Some unusual reactions of dimethyldioxirane (DMD) with flavonoid compounds

Tetrahedron

Volumn 53, Issue 25, 1997, Pages 8491-8500

  Burke, Anthony J ^a   O'Sullivan, W Ivo ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

FLAVONOID;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; TEMPERATURE;

ARENE;

EID: 0030957059     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00506-1     Document Type: Article

References (27)

1. Part 19, Brady, B.A.; Geoghegan, M.; O'Sullivan, W.I. Proc. R. Ir. Acad., 1989, 89B, 105.
2. Current address: Instituto de Tecnologia Química e Biológica, Rua da Quinta Grande, 6, Apartado 127, 2780 Oeiras, Portugal (E-mail address: burke@itqb.unl.pt).
3. For main references see; (a) Murray, R.W. Chem. Rev., 1989, 89, 1187;
4. (b) Adam, W.; Curci, R.; Edwards, J.O. Acc. Chem. Res., 1989, 22, 205.
5. Adam, W.; Golsch, D.; Hadjiarapoglou, L.; Potonay, T. Tetrahedron lett., 1991, 32, 1041; idem, J. Org. Chem., 1991, 56, 7292.
6. Adam, W.; Golsch, D.; Hadjiarapoglou, L.; Potonay, T. Tetrahedron lett., 1991, 32, 1041; idem, J. Org. Chem., 1991, 56, 7292.
7. Adam., W.; Hadjarapoglou, L.; Levai, A. Synthesis, 1992, 4, 436.
8. Adam., W.; Bialas, J.; Hadjarapoglou, L.; Potonay, T. Synthesis, 1992, 1, 49.
9. 2-Arylmethylenebenzo[b]furan-3(2H)-ones have the trivial name aurone which is used in the text for convenience. All the compounds described in this paper are racemates, only one enantiomer of which in each case is referred to in the text and shown in the diagrams.
10. Brady, B.A.; Geoghegan, M.; McMurtrey, K.D.; O'Sullivan, W.I. J. Chem. Soc., Perkin Trans. 1, 1981, 119.
11. This was prepared by u.v. irradiation of 1 according to the procedure of; Brady, B.A.; Kennedy, J.A.; O'Sullivan, W.I. Tetrahedron, 1973, 29, 359.
12. Brady, B.A.; Healy, M.M.; O'Sullivan, W.I. J. Chem. Soc., Perkin Trans. 1, 1983, 1151.
13. Ramakrishnan, V.T.; Kagan, J. J. Org. Chem., 1970, 35, 2898.
14. Adams, C.J.; Main, L. Tetrahedron, 1991, 47, 4979.
15. Main, L.; Old, K.B. Tetrahedron Lett., 1977, 32, 2809.
16. Baldwin, J.E. J. Chem. Soc., Chem. Commun., 1976, 734.
17. (a) Bennett, M.; Burke, A.J.; O'Sullivan, W.I. Tetrahedron, 1996, 52, 7163 and references cited therein;
18. (b) Saxena, S.; Makrandi, J.K.; Grover, S.K. Synthesis, 1981, 111.
19. Gulati, K.C.; Venkataraman, K. J. Chem. Soc., 1936, 267.
20. (a) Smith, M.A. J. Org. Chem. 1963, 28, 933;
21. (b) Utaka, M.; Takeda, A. J. Chem. Soc., Chem. Commun., 1985, 1824.
22. The details of the synthesis and determination of the configuration of this compound will be published later.
23. The dimethyldioxirane-acetone solution used here was wet (ca. 1-2% water, Eaton, P.E.; Wicks, G.E., J. Org. Chem. 1988, 53, 5353). i.e. it had not been pretreated with any drying agent and this was the general practice for most of the dimethyldioxirane-acetone solutions used in the experiments detailed in this paper. The reason for this was that anhydrous magnesium sulphate led to some decomposition of the DMD, an observation in agreement with that of Chenault and Danishefsky (Chenault, H.K.; Danishefsky, S.J. J. Org. Chem., 1989, 54, 4249), consequently anhydrous potassium carbonate was avoided because of possible base catalysed decomposition. Another observation was that, standing the DMD-acetone solution over molecular sieves (4A) for several days at -20°C led to a reduction in the concentration of the DMD solution to half its original concentration.
24. The dimethyldioxirane-acetone solution used here was wet (ca. 1-2% water, Eaton, P.E.; Wicks, G.E., J. Org. Chem. 1988, 53, 5353). i.e. it had not been pretreated with any drying agent and this was the general practice for most of the dimethyldioxirane-acetone solutions used in the experiments detailed in this paper. The reason for this was that anhydrous magnesium sulphate led to some decomposition of the DMD, an observation in agreement with that of Chenault and Danishefsky (Chenault, H.K.; Danishefsky, S.J. J. Org. Chem., 1989, 54, 4249), consequently anhydrous potassium carbonate was avoided because of possible base catalysed decomposition. Another observation was that, standing the DMD-acetone solution over molecular sieves (4A) for several days at -20°C led to a reduction in the concentration of the DMD solution to half its original concentration.
25. Previously dried over molecular sieves (4A).
26. Feurstein, W.; Kostanecki, St.V. Ber., 1898, 31, 710.
27. Saxena, S.; Jain, P.K.; Makrandi, J.K.; Grover, S.K. Tetrahedron Lett., 1983, 24, 3401.