Stereocontrolled synthesis of piperidine alkaloids, (−)-241D and (−)-isosolenopsin |
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Authors: | RVNS MuraliS Chandrasekhar |
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Institution: | Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India |
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Abstract: | Highly diastereocontrolled synthesis of alkaloids, (−)-241D and (−)-isosolenopsin was achieved in 7.7% and 5.3% yields, respectively, using a Barbier-type allylation of a chiral imine and d-proline catalyzed aldol addition reaction of a β-amino aldehyde with acetone as the key steps. The synthesis involves a nine-step sequence using (S)-valinate imine in a Barbier-type allylation for the first time. |
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Keywords: | Alkaloids Isosolenopsin Barbier-type allylation Aldol addition β-Amino aldehyde (S)-Valinate imine |
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