PURPOSE: To prepare the titled compounds (some of which are novel) from a hydroquinone derivative or a quinone derivative, etc., by chemically modifying the double bond of the terminal prenyl group selectively, introducing a functional group to the terminal methyl group of the resulted novel intermediate, and then introducing isoprenyl unit to the produced compound.
CONSTITUTION: The terminal prenyl group of the compound of formula I or II (R1 is methyl, methoxy, or two R1 may together from -CH=CH-CH=CH-; Z is protecting group; n is 1W9) is epoxidized to obtain a novel epoxy derivative. Opening of the epoxy group of the derivative gives a novel allyl alcohol derivative, which is (when it is quinone derivative, after converting to the hydroquinone derivative) halogenated to obtain a novel halogenohydroquinone derivative of formula III. The compound of formula III is made to react with a prenyl derivative of formula IV (Y is arylthio, etc.; ni is 1W9). The objective compound of formula VI or formula VII is obtained by the reductive elemination of the group Y from the novel compound of formula V obtained by the above reaction, and if necessary, the removal of the protecting group and/or the oxidation.
KATOU KANEYOSHI