Synfacts 2020; 16(09): 1011
DOI: 10.1055/s-0040-1705829
Synthesis of Natural Products and Potential Drugs

Synthesis of (–)-Chilocorine C

Erick M. Carreira
Fabian Glatz
Lisnyak VG, Snyder SA. * The University of Chicago, USA
A Concise, Enantiospecific Total Synthesis of Chilocorine C Fueled by a Reductive Cyclization/Mannich Reaction Cascade.

J. Am. Chem. Soc. 2020;
142: 12027-12033


Snyder and co-workers reported the asymmetric total synthesis of (–)-chilocorine C, a defensive alkaloid isolated from ladybugs. Key to the synthesis was a reductive cyclization/Mannich cascade.



Advanced intermediate G, prepared by a [3+2] cycloaddition, is rapidly converted into I containing the tricyclic core of the natural product. Hofmann rearrangement followed by oxidation and aldol condensation leads to O, which is transformed into the natural product in two steps.


Publication History

Publication Date:
18 August 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany