RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000131.xml
Synfacts 2020; 16(09): 1011
DOI: 10.1055/s-0040-1705829
DOI: 10.1055/s-0040-1705829
Synthesis of Natural Products and Potential Drugs
Synthesis of (–)-Chilocorine C
Key words
(–)-chilocorine C - [3+2] cycloaddition - cascade reaction - Mannich reaction - Hofmann rearrange-mentSignificance
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
© 2020. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany