Flavonoid epoxides. Part 22. Establishment of the configuration of the diastereomeric solvolysis products of 2-arylmethylenebenzo[b]furan-3(2H)-one (aurone) epoxides

Tetrahedron

Volumn 54, Issue 10, 1998, Pages 2169-2180

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

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

^b INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

2 ARYLMETHYLENEBENZO(B)FURAN 3(2H) ONE; AURONE EPOXIDE; EPOXIDE; FLAVONOID; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; DIASTEREOISOMER; DRUG SYNTHESIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TEMPERATURE;

EID: 0032485475     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10429-X     Document Type: Article

References (23)

1. 1. Part 21, Brady, B.A.; Burke, A.J.; Schmalle, H.W.; O'Sullivun, W.I. J. Chem. Soc., Perkin Trans I, in Press.
2. 3. Brady, B.A.; Geoghegan, M.; O'Sullivan, W.I. J. Chem. Soc., Perkin Trans. 1 1989, 1557.
3. 4. 2-Arylmethylenebenzo[b]furan-3(2H)-one has the trivial name aurone which is used in the text for convenience. The aurone epoxides and their derivatives described in this paper are racemates, only one enantiomer of which in each case is refered to in the text and shown in the diagrams.
4. 5. The prefix erythro is used to denote αR,βS stereochemistry, whilst the prefix threo will be used to denote the αS,βS stereochemistry, but this nomenclature is reversed in the case of the acetoxy derivatives 11-14.
5. 6. Buchanan, J.G.; Sable, H.Z. in Selective Organic Transformation, Thyagarajan, B.S. Ed., Wiley-Interscience: New York, 1972; vol. 2, and references cited therein.
6. 7. Brady, B.A.; Kennedy, J.A.; O'Sullivan, W.I. Tetrahedron, 1973, 29, 359.
7. 8. Purification of commercial mCPBA (55-65%) was facilitated by leaving it stand under vacuum (@ 0.1 Torr) over anhydrous calcium sulphate for several days. The concentration was determined iodometrically; McDonald, R.N.; Steppel, R.N.; Dorsey, J.E.; in Organic Synthesis, Breslow, R. (ed.), John Wiley and Sons, Inc., 1970, vol 50, p 15.
8. 9. Brady, B.A.; Healy, M.M.; O'Sullivan, W.I. J. Chem. Soc., Perkin Trans. 1 1983, 1151.
9. 10. Burke, A.J.; O'Sullivan, W.I. Tetrahedron, 1997, 53, 8491.
10. 11. Brady, B.A.; Geoghegan, M; McMurtrey, K.D.; O'Sullivan, W.I. J. Chem. Soc., Perkin Trans. 1 1981, 119.
11. 12. (a) Hunter, C.A.; Saunders, J.K.M. J. Am. Chem. Soc., 1990, 112, 5525;
12. (b) Pridgen, L.N.; Abdel-Magid, A.; Lantos, I. Tetrahedron Lett. 1989, 30, 5539, these authors also stress that boat-like transition states in certain cases are known to be the principle pathway in aldol reactions, references cited therein.
13. 13. Swiss, K.A.; Choi, W-B.; Liotta, D.C.; J. Org. Chem., 1991, 56, 5978.
14. 14. BMDA has been found to effect the self-condensation of both ketones and esters: Krafft, M.E.; Holton, R.A. Tetrahedron Lett., 1983, 24, 1345; Frostick Jr., F.C.; Hauser, C.R. J. Am. Chem. Soc., 1949, 71, 1350.
15. 14. BMDA has been found to effect the self-condensation of both ketones and esters: Krafft, M.E.; Holton, R.A. Tetrahedron Lett., 1983, 24, 1345; Frostick Jr., F.C.; Hauser, C.R. J. Am. Chem. Soc., 1949, 71, 1350.
16. 15. Antus, S.; Baitz-Gács, E.; Boross, F.; Nógrádi, M.; Sólyom, A. Liebigs Ann. Chem., 1980, 1271.
17. 16. The authors (ref. 15) did not show how they differentiated between the two configurations.
18. 17. However, the difference for both pairs of isomers 15a, 15b and 16a, 16b was 0.10 ppm.
19. 18. Bennett, M.; Burke, A.J.; O'Sullivan, W.I. Tetrahedron, 1996, 52, 7163.
20. 19. Pretsch, E.; Clerc, T.; Seibl, J.; Simon, W. Spectral Data for Structural Determination of Organic Compounds, Springer-Verlag, 1983, second edition.
21. 1H nmr spectroscopy.
22. 21. Auwers, K.V.; Pohl, P. Annalen, 1915, 405, 243.
23. 22. Chemical abstracts, 1925, 19, 2047.