39 ミカン科に存在する一連の新Phenylpropanoid類 : Cuspidiol,Boninenal,Methyl Boninenalate

概要

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Three new monomeric phenylpropanoids having an isoprene unit in their molecule were isolated from Xanthoxylum (Fagara) plants (Rutaceae) and their structures were well established. Cuspidiol (1): Colourless needles, C_<14>H_<20>O_3, mp 65-67°, was obtained from the bark of X. cuspidatum as a main component. The inspection of spectral data of it and its some derivatives suggested the structure of cuspidiol as the formula (1). Total synthesis of cuspidiol was also performed via condensation of methyl 4-bromotiglate (14) having an E-configuration about the double bond with dihydro-p-coumarylalcohol(7). Boninenal (16) and Methyl Boninenalate (17): These two phenylpropanoids were isolated from X. inerme (Fagara boninensis) as colourless prisms, C_<14>H_<16>O_3, mp 95-97.5° and colourless prisms, C_<15>H_<16>O_4, mp 180° (softened at 107°). Although the isolated amounts of them were so minute that we could measured several spectral data, but taking into account that these substances could be structurally related with cuspidiol, their structures were supposed to be as the formulae (16) and (17). The validity of this assumption was shown by total syntheses of them.
天然有機化合物討論会の論文
1979-09-20