Asymmetric Synthesis of (+)-2-epi-α-Allokainic Acid Employing Ketopinic Amide as Chiral Auxiliary
碩士 === 國立清華大學 === 化學系 === 103 === This thesis deals with the application of camphor-derived ketopinic amide 139 as a chiral auxiliary in the synthesis of pyrrolidine alkaloids. Asymmetric 1,4-addition of chiral imine 116, derived from glycinate 142 and ketopinic amide 139, with α,β-unsaturated ester...
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| Format: | Others |
| Language: | zh-TW |
| Published: |
2015
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| Online Access: | http://ndltd.ncl.edu.tw/handle/g56v6u |
| Summary: | 碩士 === 國立清華大學 === 化學系 === 103 === This thesis deals with the application of camphor-derived ketopinic amide 139 as a chiral auxiliary in the synthesis of pyrrolidine alkaloids. Asymmetric 1,4-addition of chiral imine 116, derived from glycinate 142 and ketopinic amide 139, with α,β-unsaturated ester 142 afforded adduct 130 as a single isomer. Transamination of compound 130, followed by cyclization provided lactam 147. The construction of C4 stereogenic center was achieved by the aldol reaction of boc-protected lactam 147 with acetone. Further functional group transformation led to the synthesis of (+)-2- epi-α-Allokainic acid 128.
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