Synthesis and lipase-mediated stereoselective deacetylation of (±)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones

Six (+/-)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones have been synthesized in four steps starting with the coupling of resorcinol with corresponding aliphatic acid leading to the formation of 2,4-dihydroxyphenyl alkyl ketones, which upon monomethylation and hydroxymethylation, followed by acetylation afforded the racemic acetoxymethylated compounds in 17-30% overall yields. Candida rugosa lipase-catalyzed deacetylation of (+/-)-3-acetoxymethylchromanones in diisopropyl ether exhibited fairly moderate enantioselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.