天然物Majusculone, Laurencenone C, 和alpha-Chamigrene的全合成研究

• Main Authors: Bing-Chiuan Juo, 卓炳銓
• Other Authors: Day-Shin Hsu
• Format: Others
• Language: zh-TW
• Published: 2012
• Online Access: http://ndltd.ncl.edu.tw/handle/06066683998778242034

碩士 === 國立中正大學 === 化學暨生物化學研究所 === 100 === This thesis describes the total syntheses of -chamigrene (1), majusculone (2) and laurencenone C (3). We used commercially available 2,6-dimethylcyclohexanone and diethyl-1,3-acetonedicarboxylate as the starting materials in the synthesis. The allylical alchol 101 was prepared via a 1,2-addition of the lithium reagent derived from 100 and 69. SmI2 mediated reductive cyclization of 103 was used to construct the spiro[5.5]undecane skeleton. Hemiketal 104 was then reduced with LAH followed by treatment with amberlyst-15 in refluxing benzene afforded enone 110. Finally, the total syntheses of majusculone (2) was accomplished by mean of allylic oxidation of 110 .