Preparation of (Z)-3-acetoxy-5-carbomethoxy-l-cyclohexene

概要

論文の詳細を見る
(Z)-3-Acetoxy-5-carbomethoxy-l-cyclohexene was prepared via according to the reported procedures. Thus, iodolactonization of (rac)-3-cyclohexene-l-carboxylic acid followed by elimination of iodide with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave the unsaturated lactone in 86% yield for 2 steps. Alcoholysis of the obtained lactone with sodium methoxide in methanol afforded (Z)-5-carbomethoxy-3-hydroxy-1-cyclohexene in 95% yield with sole isomer. Acetylation of the alcohol 4 was carried out with AcCl and pyridine in CH_2CI_2 at 0 ℃ for 40 min to give (Z)-3-acetoxyl-5-carbomethoxy-l-cyclohexene in 22% yield with a mixture of 88% Z-isomer and 12% E-isomer.
琉球大学理学部の論文