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Total Synthesis of (+)-Isatisine A


  • We thank the Natural Sciences and Engineering Research Council (NSERC) and Merck Frosst for funding. We are grateful to Doug Hairsine for performing MS analyses. A.K. is the recipient of an OGS postgraduate scholarship. A special thanks to Dr. Jeffrey Manthorpe for helpful discussion and suggestions.


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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.