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  • Enantioselective total synthesis of (S)-bisoranjidiol, an axially chiral bisanthraquinone.

Enantioselective total synthesis of (S)-bisoranjidiol, an axially chiral bisanthraquinone.

Organic letters (2012-03-01)
Erin E Podlesny, Marisa C Kozlowski
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2-Naphthol, 99%
Sigma-Aldrich
2-Naphthol, 98%
Sigma-Aldrich
2-Naphthol, fluorescence indicator, ≥99.0%
Sigma-Aldrich
2-Naphthol, BioXtra, ≥99.0% (GC)