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Molecules 2005, 10(3), 552-558; doi:10.3390/10030552

Synthesis of Some Phenylpropanoid Monoglycerides via the Mitsunobu Protocol

1, 1, 2, 2 and 1,*
1 Hokkaido University, Graduate School of Agriculture, Kita-9, Nishi-9, Kita-ku, Sapporo 0608589, Japan 2 Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, "Acad. G. Bonchev" Str., bl.9, Sofia 1113, Bulgaria
* Author to whom correspondence should be addressed.
Received: 17 August 2004 / Revised: 24 January 2005 / Accepted: 28 January 2005 / Published: 31 March 2005
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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. phenylpropanoid glycerides; Mitsunobu esterification; deprotection.
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Batovska, D.I.; Kishimoto, T.; Bankova, V.S.; Kamenarska, Z.G.; Ubukata, M. Synthesis of Some Phenylpropanoid Monoglycerides via the Mitsunobu Protocol. Molecules 2005, 10, 552-558.

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