Stereoselective synthesis of flavonoids. Part 7. Poly-oxygenated β-hydroxydihydrochalcone derivatives

Epoxidation of a series of poly-oxygenated chalcones with urea-hydrogen peroxide complex in THF in the presence of DBU and poly-( l)- or -( d)-leucine, followed by TBTH/AIBN catalysed ring opening, afforded β-hydroxydihydrochalcones in moderate to high enantiomeric excess and yield. This represents...

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Bibliographic Details
Published in:Tetrahedron 1999-08, Vol.55 (32), p.9727-9736
Main Authors: Nel, Reinier J.J., van Rensburg, Hendrik, van Heerden, Pieter S., Coetzee, Johan, Ferreira, Daneel
Format: Article
Language:English
Subjects:
Chalcones
Enantioselection
Epoxidation
Flavonoids
Oxiranes
Regioselection
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Summary:Epoxidation of a series of poly-oxygenated chalcones with urea-hydrogen peroxide complex in THF in the presence of DBU and poly-( l)- or -( d)-leucine, followed by TBTH/AIBN catalysed ring opening, afforded β-hydroxydihydrochalcones in moderate to high enantiomeric excess and yield. This represents the first stereoselective route towards this group of flavonoids. Epoxidation of a series of poly-oxygenated chalcones with urea-hydrogen peroxide complex in THF in the presence of DBU andpoly-(L)-or-(D)-leucine, followed by TBTH/AIBN catalysed ring opening, afforded β-hydroxydihydrochalcones in moderate to high enantiomeric excess and yield. This represents the first stereoselective access to this group of flavonoids [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(99)00554-2