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- Title
Total Synthesis of Limonin.
- Authors
Yamashita, Shuji; Naruko, Akito; Nakazawa, Yuki; Zhao, Le; Hayashi, Yujiro; Hirama, Masahiro
- 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.
- Subjects
LIMONOIDS; TRITERPENES; RING formation (Chemistry); ANDROSTANE; BAEYER-Villiger rearrangement; X-ray diffraction
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 29, p8538
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201503794