4.4 Article

Concise Total Synthesis of (+)-Aphanorphine

Journal

SYNLETT
Volume 32, Issue 9, Pages 913-916

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1610769

Keywords

aphanorphine; total synthesis; alkaloids; tert-butanesulfinimine; cycloaddition; hydrogen-atom transfer

Funding

  1. Natural Science Foundation of Shandong Province [ZR2018PB006]

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A concise total synthesis of (+)-aphanorphine was achieved in six steps, utilizing key features such as Pd-catalyzed intermolecular trimethylenemethane [3+2]-cycloaddition for forming ring C and Co-catalyzed radical cyclization through hydrogen-atom transfer to close ring B.
A concise total synthesis of (+)-aphanorphine is described. The key features of the strategy include a Pd-catalyzed intermolecular trimethylenemethane [3+2]-cycloaddition to form ring C and a Co-catalyzed radical cyclization through a hydrogen-atom transfer to close ring B. The synthesis was completed in six steps.

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