Abstract
Abstract Two new prenylated flavanonols (1) and (2) isolated from the roots of Maackia tenuifolia were synthesized from resacetophenone (3). Prenylation of 3 with prenyl bromide in the presence of methanolic alkali gave 3-C-prenyl resacetophenone (4a), whereas in the presence of silver oxide catalyst, afforded mainly 5-C-prenyl resacetophenone (4b). Condensation of 4a and 4b with benzaldehyde yielded chalcones (5a and 5b) which were converted into racemic epoxides (7a and 7b) after methoxymethylation and epioxidation. Cyclization of epoxides (7a and 7b) resulted in formation of racemic flavanonols (8a and 8b).
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