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Total Synthesis of Exiguamines A and B Inspired by Catecholamine Chemistry
Author(s) -
Sofiyev Vladimir,
Lumb JeanPhilip,
Volgraf Matthew,
Trauner Dirk
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103605
Subject(s) - total synthesis , chemistry , cascade , tautomer , combinatorial chemistry , ammonium , stereochemistry , organic chemistry , chromatography
Abstract The evolution of a total synthesis of the exiguamines, two structurally unusual natural products that are highly active inhibitors of indolamine‐2,3‐dioxygenase (IDO), is described. The ultimately successful strategy involves advanced cross‐coupling methodology and features a potentially biosynthetic tautomerization/electrocyclization cascade reaction that forms two heterocycles and installs a quaternary ammonium ion in a single synthetic operation.