Goniodiol的不對稱合成研究

• Main Author: 林若纯
• Other Authors: 游錫榕
• Format: Others
• Language: zh-TW
• Online Access: http://ndltd.ncl.edu.tw/handle/12940034431834925489

碩士 === 中國文化大學 === 應用化學研究所 === 93 === ABSTRACT Goniodiol is a natural product isolated from the leaves of Goniothalamus sesquipedalis (Annonaceae). It is one of styryl lactones with a 5,6-dihydro-2-pyrone structure. Many compounds with 6-substituted 5,6-dihydro-2-pyrone skeleton in nature possess variable activities. Since goniodiol has shown cytotoxic activities to several tumor cells, we attempted to synthesize optically active goniodiol in this study by asymmetric methods. In this thesis, ethyl 3-benzoylacrylate was used as the starting material, which was converted to the ketal with ethylene glycol in the presence of p-toluenesulfonic acid. The ester group was then reduced by DIBAL-H to give a primary alcohol, which was transformed into methanesulfonate by methanesulfonyl chloride and triethylamine in dichloromethane. The sulfonate was converted to the iodide with sodium iodide. The iodide reacted with lithium acetylide and then methyl chloroformate to give a propiolate ester. In the future, the olefin can be transformed into the diol by Sharpless asymmetric dihydroxy- lation. After hydrogenation by Lindlar catalyst, deprotection of the ketal, and stereoselective reduction of the carbonyl group, (+)-goniodiol will be obtained.