Stereocontrolled synthesis of (-)-galanthamine |
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Authors: | Satcharoen Vachiraporn McLean Neville J Kemp Stephen C Camp Nicholas P Brown Richard C D |
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Institution: | School of Chemistry, University of Southampton, Highfield, Southampton, UK. |
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Abstract: | An enantioselective synthesis of (-)-galanthamine has been realized in 11 linear steps starting from isovanillin. A Mitsunobu aryl ether forming reaction was used to assemble the galanthamine backbone, which was stitched together using enyne ring-closing metathesis, Heck, and N-alkylation reactions affording the tetracyclic ring system. Control of relative and absolute stereochemistry was derived from an easily accessible enantiomerically enriched propargylic alcohol 13. |
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