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

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.

SUBMITTER: Podlesny EE

PROVIDER: S-EPMC3306814 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature

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

Podlesny Erin E EE Kozlowski Marisa C MC

Organic letters 20120224 6

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. ...[more]

PMID: 22360604

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