Download PDF
Synfacts 2018; 14(05): 0445
DOI: 10.1055/s-0037-1609840
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Seven Indole Alkaloids

Contributor(s):
Erick M. Carreira
,
Philipp Sondermann
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;
Search in Google Scholar
Further Information

Publication History

Publication Date:
17 April 2018 (online)

 
 PDF Download Permissions and Reprints

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.


#

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.


#
#


   Permissions and Reprints