Biomimetic asymmetric synthesis of (R)-GTRI-02 and (3S,4R)-3,4-dihydroxy-3,4-dihydronaphthalen-1(2H)-ones.
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.
Institute of Pharmaceutical Sciences, Albert-Ludwigs-University of Freiburg , Albertstrasse 25, 79104 Freiburg, Germany, and Institute for Inorganic and Analytical Chemistry, Albert-Ludwigs-University of Freiburg , Albertstrasse 21, 79104 Freiburg, Germany.
Syed Masood
SM
Husain
Michael A
MA
Schätzle
Caroline
C
Röhr
Steffen
S
Lüdeke
Michael
M
Müller
D053626:Atovaquone / Q000737:chemistry*; D032701:Biomimetics; D005656:Fungal Proteins / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry*; D044925:Oxidoreductases Acting on CH-CH Group Donors / Q000737:chemistry*; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000737:chemistry*
C588259:1-(3,6,8-trihydroxy-1-methylnaphthalen-2-yl)ethanone; D005656:Fungal Proteins; C116835:GTRI 02; D009281:Naphthalenes; D009284:Naphthols; D013764:Tetrahydronaphthalenes; C086024:tetrahydroxynaphthalene reductase; D044925:Oxidoreductases Acting on CH-CH Group Donors; D053626:Atovaquone