Development of the Ireland-Claisen Rearrangement of allyl glycolates, and their application to the synthesis of trans-3-hydroxy-4-hydroxymethylpyrrolidine

• Main Authors: Luo, Ching-Zong, 羅慶宗
• Other Authors: Hon, Yung-Son
• Format: Others
• Language: zh-TW
• Published: 2011
• Online Access: http://ndltd.ncl.edu.tw/handle/72821479014692751114

碩士 === 國立中正大學 === 化學暨生物化學研究所 === 99 === Through Ireland-Claisen rearrangement reaction, we have developed a series of methodologies in cis-allyl glycolate of compound A and trans-allyl glycolate of compound B. From the result, when we changed the substituent group of R1 and R2, the stereoselectivity is influenced. We used compound 164b to get compound 171 through Ireland-Claisen rearrangement reaction, then we used deprotection reaction and cyclization reaction to get compound 181. Finally, we got the biological activity compound 198, trans-3-Hydroxy-4-Hydroxymethylpyrrolidine, by oxidative cleavage reaction, reduction reaction, and deprotection reaction.