The study in copper(II) chloride-mediated one pot three-step syntheses of benzo[b]furan derivatives and its application for the total synthesis of antimicrobial molecular

• Main Authors: Chien-Liang Liu, 劉健良
• Other Authors: Yao-Jung Chen
• Format: Others
• Language: zh-TW
• Published: 2012
• Online Access: http://ndltd.ncl.edu.tw/handle/03492873832870849922

碩士 === 國立中興大學 === 化學系所 === 100 === Copper(II) chloride has been successfully used as the medium to one-pot three-steps synthesis of benzo[b]furan derivatives. A palladium-free and ligand-free reaction condition for Sonogashira- type coupling has been developed, this catalytic system is cheap and easily removed, and provide a good yield. Total synthesis of antimicrobial molecule was accomplished in six steps. This novel route was starting from the 4-methylanisole 64. The iodination of compound 64 by treating with NIS in the presence of TMSCl can provide the 90% yield. After the copper(II) chloride promoted one-pot three-step reactions of iodoanisole 28 as the key step for the construction of benzo[b]furan skeleton 63, the further steps were carried out through Grignard reagent addition and hydrolysis reaction to afford the antimicrobial molecule.