Synthesis of the monoterpene lactone from Chrysanthemum flosculosum L.

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概要

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• The synthesis of a lactonic constituent [(<I>Z</I>)-5-ethylidene-5,6-dihydro-3,6,6-trimethyl-2<I>H</I>-pyran-2-one] isolated from <I>Chrysanthemum flosculosum</I> L. is described. Dehydration of 5-ethyl-5,6-dihydro-5-hydroxy-3,6,6-trimethyl-2<I>H</I>-pyran-2-one derived from 5-ethyl-5,6-dihydro-6,6-dimethyl-3-phenylthio-2<I>H</I>-pyran-2-one <I>via</I> methylation, oxidation, [2,3]sigmatropic rearrangement, and saponification, gave the geoisomeric [(<I>E</I>)-5-ethylidene] lactone. Photochemical isomerization of the ethylidene side-chain furnished the natural lactone. The geometry of the ethylidene group in both isomers has been rigorously established.

• 公益社団法人 日本化学会の論文

著者

• Uda Hisashi

  Chemical Research Institute Of Non-aqueous Solutions Tohoku University

• Kosugi Hiroshi

  Chemical Research Institute of Non-aqueous Solutions, Tohoku University

• Yamagiwa Shûichi

  Chemical Research Institute of Non-Aqueous Solutions, Tohoku University

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