Biomimetic Asymmetric Synthesis of (R)-GTRI-02 and (3S,4R)-3,4-Dihydroxy-3,4-dihydronaphthalen-1(2H)-ones

被引：28

作者：

Husain, Syed Masood ^{[1
]}

Schaetzle, Michael A. ^{[1
]}

Roehr, Caroline ^{[2
]}

Luedeke, Steffen ^{[1
]}

Mueller, Michael ^{[1
]}

机构：

[1] Univ Freiburg, Inst Pharmaceut Sci, D-79104 Freiburg, Germany

[2] Univ Freiburg, Inst Inorgan & Analyt Chem, D-79104 Freiburg, Germany

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 14期

关键词：

SECONDARY MOLD METABOLITES; MELANIN BIOSYNTHESIS; MAGNAPORTHE-GRISEA; INHIBITOR; REDUCTASE;

D O I：

10.1021/ol301305p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3600 / 3603

页数：4

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