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

Synthesis of (–)-Chilocorine C

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
 

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.


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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.


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Publication History

Publication Date:
18 August 2020 (online)

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