Synthetic studies of Fawcettimine precursor

• Main Authors: Lia Deng-Yu, 賴登郁
• Other Authors: Lee Yean-Jang
• Format: Others
• Language: zh-TW
• Online Access: http://ndltd.ncl.edu.tw/handle/93958601733577390637

碩士 === 國立彰化師範大學 === 化學系 === 103 === This there dealt with the synthesis of (9aS, 11R, 13aS)-11-methyl-2,3,4,5,6,7,9a,10,11,12–decahydro-1H -indeno[1,7a-e]azonin-13(9H)-one framework of fawcettimine. In our achievement, we have two methods to get the starting material 5-methyl cyclohexenone. We obtain the racemic 5-methyl cyclohexenone (5) by ethyl acetoacetate and crotonaldehyde, and obtain the single configurational (R)-5-methyl cyclohexenone (9) by Caine’s strategy. Then synthesis of the intermediate N-tosyl cyclohexenone 3 is achieved by Suzuki coupling reaction. On the other hand, we refer the reference about the TMS-cyclopentene annulations that Danheiser published, and obtain (trimethylsilyl) allene 4 we would want successfully. After obtain required N-tosyl cyclohexenone 3 and (trimethylsilyl) allene 4, we have begun to study the TMS-cyclopentene annulations ([3+2] cyclization) to construct the framework.