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

Synthesis of (–)-Chilocorine C

Autoren

    Rezensent(en):

  • 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
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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.




Publikationsverlauf

Artikel online veröffentlicht:
18. August 2020

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