Synthesis of some phenylpropanoid monoglycerides via the Mitsunobu protocol.
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.
Batovska
Daniela I
DI
Hokkaido University, Graduate School of Agriculture, Kita-9, Nishi-9, Kita-ku, Sapporo 0608589, Japan.
Kishimoto
Takao
T
Bankova
Vassya S
VS
Kamenarska
Zornitsa G
ZG
Ubukata
Makoto
M
D002934:Cinnamates; D003373:Coumaric Acids; D004952:Esters; D007202:Indicators and Reagents; D007700:Kinetics; D008958:Models, Molecular; D050178:Monoglycerides / Q000138:chemical synthesis*; D010636:Phenols; D011407:Propane
D002934:Cinnamates; D003373:Coumaric Acids; D004952:Esters; D007202:Indicators and Reagents; D050178:Monoglycerides; D010636:Phenols; C029010:cinnamic acid; C004999:ferulic acid; D011407:Propane