DOI: 10.1002/ange.202316016 ISSN: 0044-8249
Asymmetric Synthesis of Arboduridine
Rui Yang, Zeyu Zhou, Huanfeng Jiang, Toh-Seok Kam, Kai Chen, Zhiqiang Ma- General Medicine
The first asymmetric total synthesis of the monoterpenoid indole alkaloid arboduridine has been accomplished. The tricyclic A/B/D ring system is constructed by an enantioselective Michael reaction followed by intramolecular nucleophilic addition. Intramolecular α‐amination of ketone is employed to forge the piperidine ring, while a Horner‐Wadsworth‐Emmons (HWE) reaction is used to form the pyrrolidine ring. A reduction cyclization cascade leads to formation of the tetrahydrofuran ring.