Asymmetric Synthesis of Arboduridine

作者：Yang, Rui; Zhou, Zeyu; Jiang, Huanfeng; Kam, Toh-Seok; Chen, Kai; Ma, Zhiqiang^*

来源：Angewandte Chemie - International Edition, 2023.

DOI：10.1002/anie.202316016

• Asymmetric Catalysis
• Michael Addition
• Monoterpenoid Indole Alkaloids
• Total Synthesis

The first asymmetric total synthesis of the monoterpenoid indole alkaloid arboduridine has been accomplished. The tricyclic A/B/D ring system was constructed by an enantioselective Michael reaction followed by intramolecular nucleophilic addition. Intramolecular alpha-amination of a ketone forged the piperidine ring, while a Horner-Wadsworth-Emmons (HWE) reaction was used to form the pyrrolidine ring. A reduction cyclization cascade led to formation of the tetrahydrofuran ring. @@@ Asymmetric total synthesis of the monoterpenoid indole alkaloid arboduridine has been accomplished. The synthesis features a highly enantioselective Michael addition to establish the vicinal sterically congested quaternary C7 and tertiary C19 stereocenters. The other stereogenic centers in this core unit were installed in a stereospecific and sequential fashion by taking advantage of the conformations of the corresponding precursors.+image

• 单位
  北京大学