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Biomimetic Asymmetric Synthesis of (R)-GTRI-02 and (3S,4R)-3,4-Dihydroxy-3,4-dihydronaphthalen-1(2H)-ones
- Husain, Syed Masood, Schätzle, Michael A., Röhr, Caroline, Lüdeke, Steffen, Müller, Michael
- Organic letters 2012 v.14 no.14 pp. 3600-3603
- Magnaporthe grisea, biomimetic synthesis, biomimetics, chemical reactions, chemical structure, organic compounds, stereoselectivity
- The NADPH-dependent tetrahydroxynaphthalene reductase (T₄HNR) from Magnaporthe grisea was used for the biomimetic synthesis of (R)-GTRI-02 by stereoselective reduction of 1-(3,6,8-trihydroxy-1-methylnaphthalen-2-yl)ethanone. This also led to the isolation of a (3S,4R)-cis-ketodiol formed by T₄HNR-catalyzed reduction of the corresponding hydroxynaphthoquinone. Flaviolin and lawsone also reduced to corresponding cis-ketodiols in good yields.