8Z, 11E, 13Z型トリエニル側鎖を有するウルシオールジメチルエーテルの合成

抄録

Dimethyl ether derivative (6) of 3- (8 Z, 11 E, 13 Z-pentadecatrienyl) catechol (5) was prepared. Compound (5) in Japanese Lac, the sap of Rhus vernicifera, was confirmed to be present by a comparison of gas chromatographic retention time of the dimethyl ether (6) with that of the methylated derivative of the natural product. In the synthetic route to the targed compound (6), the double bond with Z configuration at position 8 in the side chain was constructed by a Wittig reaction between the aldehyde (7) and ylide from the C₇-dienyl phosphonium salt (8) (Fig.-2). The phosphonium salt (8) was synthesized from 3-butyn-1-ol (9) via 8 steps as shown in Fig.-3.