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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201711535
Subject(s) - atropisomer , chemistry , annulation , quinone , total synthesis , naphthoquinone , monomer , natural product , nucleophile , condensation , nucleophilic addition , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , polymer , physics , thermodynamics
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.