Divergent Synthesis of Skeletally Distinct Arboridinine and Arborisidine

Autor:	Yuecheng Wu, Zhiqiang Ma, Yubing Pang, Cheng Wang, Nanping Zhang, Ting Fan, Rui Yang, Pengquan Chen, Xue-Tao Xu, Ying Li, Toh-Seok Kam, Huanfeng Jiang
Rok vydání:	2021
Předmět:	chemistry.chemical_classification Ketone Stereochemistry Total synthesis Arboridinine General Chemistry General Medicine Catalysis Nucleophile chemistry Intramolecular force Divergent synthesis Mannich reaction Peterson olefination
Zdroj:	Angewandte Chemie. 133:27184-27191
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.202110149
Popis:	A divergent synthesis of skeletally distinct arboridinine and arborisidine was achieved. The central divergent strategy was inspired by the divergent biosynthetic cyclization mode of arboridinine and arborisidine and their hidden topological connection. The branch point was reached through a Michael and Mannich cascade process. A site-selective intramolecular Mannich reaction was developed to construct the tetracyclic core of arboridinine, while a site-selective intramolecular α-amination of ketone was used to access the tetracyclic core of arborisidine. A strategic Peterson olefination through intramolecular nucleophile delivery was able to set up the exocyclic olefin of arboridinine.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1a61d36fccc76bdffdd810e5c8b298fb https://doi.org/10.1002/ange.202110149 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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