Total Synthesis of (+)-Isatisine A

Total Synthesis of (+)-Isatisine A

Isatis indigotica has long been used as a source of therapeutic compounds in traditional Chinese medicine (the roots are the source of Ben Lan Gen herbal tea). In 2007 the leaves of I. indigotica yielded isatisine A, an unusual oxidized bis‐indole. A concise, enantiospecific total synthesis of isati...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2010-02, Vol.49 (6), p.1133-1135
Hauptverfasser: Karadeolian, Avedis, Kerr, Michael A
Format: Artikel
Sprache:eng
Schlagworte:
alkaloids
asymmetric synthesis
heterocycles
Indole Alkaloids - chemical synthesis
Isatin - analogs & derivatives
Isatin - chemical synthesis
isatisine A
Molecular Structure
Oxidation-Reduction
Stereoisomerism
total synthesis
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Zusammenfassung:Isatis indigotica has long been used as a source of therapeutic compounds in traditional Chinese medicine (the roots are the source of Ben Lan Gen herbal tea). In 2007 the leaves of I. indigotica yielded isatisine A, an unusual oxidized bis‐indole. A concise, enantiospecific total synthesis of isatisine A is reported using a homochiral cyclopropane diester to construct the key tetrahydrofuran ring.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200906632