合成路线1

In a different strategy, 3-methoxysalicylaldehyde (VII) was protected as the silyl ether (VIII) using t-butyldimethylsilyl chloride and Et3N. Wittig reaction of aldehyde (VIII) with (9-hydroxynonyl)triphenylphosphonium bromide (IX) afforded olefin (X). This was alternatively prepared by addition of Grignard reagent (XI) to the aldehyde (VIII) to give carbinol (XII), which was further subjected to dehydration and acetal hydrolysis under acidic conditions to afford (X). Catalytic hydrogenation of olefin (X) furnished the 10-aryl decanol (XIII). The heptadecenyl side chain of (XVI) was then constructed by Swern oxidation of alcohol (XIII) to the corresponding aldehyde (XIV), followed by Wittig reaction with heptyltriphenylphosphonium bromide (XV). Desilylation of (XVI) with tetrabutylammonium fluoride gave the phenol precursor (VI), which was finally oxidized to the desired quinone by the same method as above.