Achiral auxiliary-assisted chiral transfer via microwave-accelerated aza-Claisen rearrangement: a short synthesis of (+)-1-hydroxyquinolizidinone |
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| Authors: | Jaehoon SimHwayoung Yun Jong-Wha JungSujin Lee Nam-Jung KimYoung-Ger Suh |
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| Institution: | a College of Pharmacy, Seoul National University, Seoul 151-742, Republic of Korea
b College of Pharmacy, Kyungpook National University, Daegu 702-701, Republic of Korea |
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| Abstract: | A short and efficient synthesis of (+)-1-hydroxyquinolizidinone as an advanced core intermediate for the syntheses of (+)-epiquinamide, (+)-homopumiliotoxin, and (+)-lupinine is described. The key feature of our strategy includes a sequential chiral transfer using an achiral phenylsulfide auxiliary via microwave-accelerated aza-Claisen rearrangement of the unexplored N-thiophenoxyacetyl-α-vinyl piperidine substrate and the oxone-induced transannulation. |
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| Keywords: | (+)-1-Hydroxyquinolizidinone Quinolizidine alkaloid aza-Claisen rearrangement Transannulation Achiral auxiliary |
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