Synthetic studies towards faveline methyl ether

• Main Authors: MENG-HSUAN CHIANG, 江孟軒
• Other Authors: Rong-Jie Chein
• Format: Others
• Language: zh-TW
• Published: 2011
• Online Access: http://ndltd.ncl.edu.tw/handle/66266647163359094405

碩士 === 國立中央大學 === 化學研究所 === 100 === In 1991, Professor Nozoe et al. isolated faveline methyl ether from the methanolic extracts of the bark of Favela which showed the bioactivity against P-388 lymphocytic leukemia in cell culture. There are four total syntheses of faveline methyl ether reported. In this thesis, we planned to shorten the synthetic steps by applying 5-exe-dig cyclization /Claisen rearrangement as a cyclization key step. First, 3 and 23 were synthesized in four and seven steps respectively from 9 and 33, followed by nucleophilic attack and terminal alkyne deprotection to generate intermediate 1 as a precursor of 5-exo-dig cyclization/Claisen rearrangement. Unfortunately, only compound 44 was obtained after several trials with different reaction conditions. In light of these results, we decided to apply metal catalyzed 5-exe-dig cyclization methodologys. The exploration to asymmetry synthesis was also investigated in this thesis.