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Synfacts 2018; 14(05): 0445
DOI: 10.1055/s-0037-1609840
DOI: 10.1055/s-0037-1609840
Synthesis of Natural Products and Potential Drugs
Total Synthesis of Seven Indole Alkaloids
Miloserdov FM.
Kirillova MS.
Muratore ME.
Echavarren AM.
* Institute of Chemical Research of Catalonia, Tarragona and Universitat Rovira i Virgili, Tarragona, Spain
Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship.
J. Am. Chem. Soc. 2018;
DOI: 10.1021/jacs.7b13484.
Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship.
J. Am. Chem. Soc. 2018;
DOI: 10.1021/jacs.7b13484.
Further Information
Publication History
Publication Date:
17 April 2018 (online)
Key words
Passerini reaction - photoredox catalysis - gold catalysis - indole alkaloids - pyrroloazocine motif
Significance
A set of seven indole alkaloids were synthesized by the Echavarren group through common precursor I. The alkaloids all contain a pyrroloazocine core and were shown to reverse multidrug resistance in cancer cells. Further experiments provided insights into a biosynthetic mechanism.
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Comment
The use of an imine formation–lactamization–rearrangement cascade provides rapid access to C. A set of homologations and gold cyclizations led to the desired carbon framework in I. Functional group manipulations then led to a collection of related natural products.
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