Methyl 4-Carbomethoxy-3-Hydroxy-5-Methyl-Phenyl-Acetoacetate from the Disilylated Dianion of Methyl Acetoacetate

Recently, Chaley and Chan1 reported a novel synthesis of methyl olivetolate (3a) from the annelation of 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene (1) with the acid chloride 2a and titanium tetrachloride at room temperature. In view of their success, we attempted to apply this methodology for a convenient synthesis of isotopically labelled orsellinic acid in order to unravel its biosynthesis to cyclopentanoids.