Synthesis of dihydrocoumarin carbamate derivatives

Syntheses and Biological Activities of Chroman-2-ones. A Review

“…139 Imasheva et al have used the same TFA mediated procedure for the synthesis of dihydrocoumarins with a carbamate function attached to C-6 or C-7 from meta-and parahydroxy substituted methylphenylcarbamates with cinnamic acids or esters containing electron donating substituents. 140 Condensation of dimethoxyphenol with 3,3-dimethylacrylate in methanesulfonic acid was carried out to give a dihydrocoumarin which was reduced to a diol using lithium aluminium hydride and the primary alcohol was then protected as a TBDMS ether. 141 This product was used as a coupling linker for the synthesis of cyclic prodrugs; a new pro-drug with a modified phenylpropionic acid promoiety was also prepared.…”