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Enantioselective Total Synthesis of (S)-Bisoranjidiol, an Axially Chiral Bisanthraquinone

Author:
Podlesny, Erin E., Kozlowski, Marisa C.
Source:
Organic letters 2012 v.14 no.6 pp. 1408-1411
ISSN:
1523-7052
Subject:
2-naphthol, chemical reactions, enantioselectivity, positional isomers, regioselectivity
Abstract:
The first enantioselective total synthesis of the bisanthraquinone (S)-bisoranjidiol and an unnatural regioisomer has been accomplished. Key features of the synthesis include the asymmetric oxidative biaryl coupling of a hindered 8-substituted 2-naphthol, selective para-quinone formation, and regioselective tandem Diels–Alder/aromatization reactions.
Agid:
5785010