Synthetic Studies of Sulfur-substituted Indolizidines and Quinolizidines by Ring-Closing Metathesis

• Main Authors: Lee Tse-Ming, 李澤明
• Other Authors: Chou shang-shing Peter
• Format: Others
• Language: zh-TW
• Published: 2006
• Online Access: http://ndltd.ncl.edu.tw/handle/10849947983385687012

碩士 === 輔仁大學 === 化學系 === 94 === This thesis has accomplished synthesis of new quinolizidine compounds 13 and 14 by ring-closing metathesis (RCM). Compound 10 was first converted to compound 11 , which underwent RCM to give product 13. On the other hand, compound 1a was alkylated at C-2 to give 3-sulfolene 24, which was reated with PTSI to give the cycloaddition product 26. Upon cleavage of the N-tosyl group, and attachment of the allyl group, the intermediate product 12 also underwent RCM to give quinolizidine 14, but only at much higher temperature and with lower yield. It is proposed that in the rate-determining step the different positions of the methyl group in compounds 11 and 12 had different steric hindrance with the C-6 hydrogen. Compound 13 was further oxidized by m-CPBA to compounds 22 and 23.