synthesis of some phenylpropanoid monoglycerides via the mitsunobu protocol一些phenylpropanoid合成单甘酯通过mitsunobu协议.pdfVIP

Molecules 2005, 10, 552–558 molecules ISSN 1420-3049 Synthesis of Some Phenylpropanoid Monoglycerides via the Mitsunobu Protocol Daniela I. Batovska 1, 2, Takao Kishimoto 1, Vassya S. Bankova 2, Zornitsa G. Kamenarska 2 and Makoto Ubukata 1,* 1 Hokkaido University, Graduate School of Agriculture, Kita-9, Nishi-9, Kita-ku, Sapporo 0608589, Japan; Tel./Fax: (+81)-11-706-3638 2 Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., bl.9, Sofia 1113, Bulgaria; Tel.: (+359) 2-9606-134, Fax: (+359) 2-87-700-225 * To whom correspondence should be addressed. E-mail: m-ub@for.agr.hokudai.ac.jp Received: 17 August 2004; in revised form: 24 January 2005 / Accepted: 28 January 2005 / Published: 31 March 2005 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. Introduction Phenylpropanoid glycerides are found as minor components in propolis and different Liliacea, Juncaceae, and Gramineae plant species [1-5]. Some of them possess interesting biological properties, such as antialgal [4], antitumor [6], and antiproliferative activities [2].