Abstract

A facile approach for the total synthesis of prenylated flavonoids, (±)-abyssinone-VI-4-O-methyl ether (1), (±)-abyssinone-IV-4'-O-methyl ether (2), (±)-abyssinone-V-4'-O-methyl ether (3) and (±)-sigmoidin E (4), has been de- scribed. The key intermediate 4-hydroxy-3,5-di-(3-methylbut-2-enyl)benzaldehyde (6) was synthesized that features regiose- lective prenylation of 4-hydroxybenzaldehyde and crystallizing with petroleum ether from the reaction mixture by freeze-out effect. All structures of new compounds were confirmed by IR, 1 H NMR, MS and HRMS techniques.

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