Synthesis of Some Phenylpropanoid Monoglycerides via the Mitsunobu Protocol

Abstract

Natural monoglycerides of cinnamic, ferulic and p-coumaric acids were synthesized in good to high overall yields from isopropylidene glycerol via the Mitsunobu reaction and further deprotection of the corresponding acetonides with Amberlyst 15. The method avoids the need of protection of the phenolic hydroxyls. During the Mitsunobu esterifications a strong influence of the acid strength on the efficacy and outcome of the reaction was observed.

Keywords

• phenylpropanoid glycerides
• Mitsunobu esterification
• deprotection.