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

Synthesis of (–)-Chilocorine C

Authors

    Contributor(s):

  • 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
CrossrefPubMedSearch in Google Scholar
Further Information
 
 PDF Download Permissions and Reprints

Key words

(–)-chilocorine C - [3+2] cycloaddition - cascade reaction - Mannich reaction - Hofmann rearrange-ment

Significance

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.


Comment

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

Article published online:
18 August 2020

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany


  Permissions and Reprints