Abstract
Limonoids are highly oxygenated C13α-triterpenes and common secondary metabolites. Several hundred congeners have been isolated to date. The first total synthesis of (±)-limonin, the flagship congener of the limonoids, is now reported and features 1) a tandem radical cyclization generating the BCD ring system with the C13α configuration that is essential to the limonoids and a Robinson annulation to construct the limonoid androstane framework, 2) a singlet-oxygen cycloaddition and a Baeyer-Villiger oxidation to synthesize the highly oxidized D ring, and 3) a Suárez reaction to construct the unique AA′ ring system.
Original language | English |
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Pages (from-to) | 8538-8541 |
Number of pages | 4 |
Journal | Angewandte Chemie - International Edition |
Volume | 54 |
Issue number | 29 |
DOIs | |
Publication status | Published - 2015 Jul 13 |
Keywords
- cycloaddition
- limonoids
- oxidation
- radical reactions
- total synthesis
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)