Synthesis of benzocoumarins from β-tetralones and the first total synthesis of natural occurring 9-hydroxy-8-methyl-3H-benzo[f]chromen-3-one

• Main Authors: Hong, Ya-Chun, 洪雅純
• Other Authors: Hon, Yung-Son
• Format: Others
• Language: zh-TW
• Published: 2011
• Online Access: http://ndltd.ncl.edu.tw/handle/79333103916235880422

碩士 === 國立中正大學 === 化學暨生物化學研究所 === 99 === We improved the synthesis of 5,6-benzocoumarin. In this thesis, we have achieved two pathways of synthesis. First, we used acetylation, dehydrogenation, and rearrangement to form 5,6-benzocoumarin (i.e., 4 →3 →2 →1). Second, we used β-tetralone to do rearrangement under acidic condition to get benzopyrone, and then we used aromatization synthesizing 5,6-benzocoumarin to form benzopyrone(i.e., 4 →6 →1). The two pathways respectively increased 30~40% yield, and we applied our methods to synthesize natural product.