Journal
SYNTHESIS-STUTTGART
Volume 44, Issue 9, Pages 1308-1314Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0031-1290756
Keywords
flavonoid; Claisen rearrangement; prenylation; Kaiho's method; flavonols; flavanones
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Funding
- Program for Promotion of Basic and Applied Researches for Innovations in Bio-oriented Industry (Japan)
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Synthesis of C8-prenylated flavonols and flavanones via the palladium-catalyzed 7-O-1,1-dimethylprop-2-enylation, followed by Claisen rearrangement is described. Two regioselectivities (carbon-carbon bond formation at either the tail or head of the prenyl group and carbon-carbon bond formation at either C8 or C6) were efficiently improved when acetic anhydride was used as a solvent instead of N,N-dimethylformamide.
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