Divergent synthesis of skeletally distinct arboridinine and arborisidine
Document Type
Article
Publication Date
12-20-2021
Abstract
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 alpha-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.
Keywords
Alkaloids, Arboridinine, Arborisidine, Divergent synthesis, Total synthesis
Divisions
CHEMISTRY
Funders
National Natural Science Foundation of China (NSFC) [Grant No: 21871098 & 22071064 & 21672073 & 21803019],National Program on Key Research Project [Grant No: 2016YFA0602900],National Natural Science Foundation of Guangdong Province [Grant No: 2017B090903003],Youth Science and Technology Talent Promotion Fund [Grant No: X20200301056],Science and Technology Program of Guangzhou [Grant No: 201707010073],Fundamental Research Funds for the Central Universities,SCUT,China Postdoctoral Science Foundation [Grant No: 2018M643063]
Publication Title
Angewandte Chemie International Edition
Volume
60
Issue
52
Publisher
John Wiley & Sons
Publisher Location
POSTFACH 101161, 69451 WEINHEIM, GERMANY