4.8 Article

A Nine-Step Formal Synthesis of (±)-Morphine

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ORGANIC LETTERS
卷 21, 期 5, 页码 1347-1349

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00044

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  1. Natural Sciences and Engineering Research Council
  2. government of Ontario
  3. government of Quebec
  4. University of Ottawa

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A nine-step stereoselective formal synthesis of (+/-)-morphine from readily available o-vanillin is presented. The carbocyclic structure of morphine was quickly assembled through an orchestration of the intermolecular Diels-Alder/Claisen/Friedel Crafts sequential reaction. This approach involves many one-pot procedures and no protecting groups, and only a few chromatographic purifications are required.

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