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Total Synthesis of Aurofusarin: Studies on the Atropisomeric Stability of Bis‐Naphthoquinones
Author(s) -
Qi Chao,
Wang Wenyu,
Reichl Kyle D.,
McNeely James,
Porco John A.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201711535
Subject(s) - atropisomer , chemistry , annulation , total synthesis , natural product , quinone , naphthoquinone , monomer , nucleophile , nucleophilic addition , condensation , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , thermodynamics , polymer , physics
Abstract An efficient annulation involving pyrone addition to a quinone and Dieckmann condensation was developed for rapid assembly of a γ‐naphthopyrone monomeric precursor to the bis‐naphthoquinone natural product aurofusarin. Dimerization was achieved through Pd II ‐catalyzed dehydrogenative coupling. Further studies employing asymmetric nucleophilic epoxidation indicate that the atropisomers of aurofusarin and derivatives are not configurationally stable at ambient temperature.