4.8 Article

Total synthesis of (±)-mitorubrinic acid

Journal

ORGANIC LETTERS
Volume 8, Issue 16, Pages 3481-3483

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol0610993

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Funding

  1. NIGMS NIH HHS [R01 GM064831-05, R01 GM064831-01, R01 GM064831-02, GM-64831, R01 GM064831-03, R01 GM064831-04, R01 GM064831] Funding Source: Medline

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(+/-)-Mitorubrinic acid, a member of the azaphilone family of natural products, has been constructed in 12 steps. Key aspects of the synthesis include elaboration and oxidative dearomatization of an isocoumarin intermediate to provide the azaphilone nucleus with a disubstituted, unsaturated carboxylic acid side chain.

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