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Total Synthesis of (−)‐Indoxamycins A and B
Author(s) -
Hu Naifeng,
Dong Changming,
Zhang Cuifang,
Liang Guangxin
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201902043
Subject(s) - stereocenter , michael reaction , olefin fiber , chemistry , quaternary carbon , tandem , total synthesis , enantioselective synthesis , combinatorial chemistry , derivative (finance) , carbon chain , stereochemistry , enantiomer , catalysis , organic chemistry , materials science , financial economics , economics , composite material
The concise total syntheses of (−)‐indoxamycins A and B is reported. The chemistry features a seven‐step preparation of a highly congested [5.5.6] tricyclic advanced common intermediate from a readily available R ‐carvone derivative. Key steps involve a Pauson–Khand reaction for the rapid construction of a basic scaffold bearing a quaternary carbon, a copper‐catalyzed Michael addition for the introduction of another adjacent all‐carbon quaternary stereocenter, and a tandem retro‐oxa‐Michael addition/1,2‐addition/oxa‐Michael addition for the installation of a trisubstituted olefin side chain. This synthetic strategy allows for easy access to both enantiomers of this family of natural products and their analogues from cost‐effective starting material through straightforward chemical transformations.