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Asymmetric Total Synthesis of (–)-Gracilamine Using a Bioinspired Approach

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The asymmetric total synthesis of optically pure (–)-gracilamine (1) was achieved by employing a bioinspired approach. The strategy involved elaboration of 3a-arylhexahydroindole 7, a designed precursor, to 3a-formylarylhexahydroindole 5, which… Click to show full abstract

The asymmetric total synthesis of optically pure (–)-gracilamine (1) was achieved by employing a bioinspired approach. The strategy involved elaboration of 3a-arylhexahydroindole 7, a designed precursor, to 3a-formylarylhexahydroindole 5, which upon heating with l-leucine ethyl ester gave (–)-1 efficiently.

Keywords: asymmetric total; total synthesis; gracilamine; bioinspired approach

Journal Title: European Journal of Organic Chemistry
Year Published: 2017

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