A concise synthesis of (±) and a total synthesis of (+)-epiquinamide |
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Authors: | Sok Teng Tong |
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Institution: | Department of Chemistry, University of Auckland, 23 Symonds St., Auckland, New Zealand |
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Abstract: | A total synthesis of the quinolizidine alkaloid (+)-epiquinamide 1 has been achieved starting from (−)-pipecolinic acid 3. The key step is the highly diastereoselective addition of a TBDMS-protected propargyl alcohol to a chiral aldehyde derived from 3 to give erythro alkynol 19, which is then easily transformed into the desired bicyclic skeleton. |
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