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Stereocontrolled Semisyntheses of Elliptone and 12aβ-Hydroxyelliptone
- Source :
- Journal of Natural Products; October 2017, Vol. 80 Issue: 10 p2751-2755, 5p
- Publication Year :
- 2017
-
Abstract
- Operationally simple, stereocontrolled semisyntheses of the anticancer rotenoids elliptone and 12aβ-hydroxyelliptone, isolated from Derris ellipticaand Derris trifoliata, respectively, are described. Inspired by the work of Singhal, elliptone was prepared from rotenone via a dihydroxylation-oxidative cleavage, chemoselective Baeyer–Villiger oxidation, and acid-catalyzed elimination sequence. Elaboration of elliptone to 12aβ-hydroxyelliptone was achieved via a diastereoselective chromium-mediated Étard-like hydroxylation. The semisynthesis of elliptone constitutes an improvement over previous methods in terms of safety, scalability, and yield, while the first synthesis of 12aβ-hydroxyelliptone is also described.
Details
- Language :
- English
- ISSN :
- 01633864 and 15206025
- Volume :
- 80
- Issue :
- 10
- Database :
- Supplemental Index
- Journal :
- Journal of Natural Products
- Publication Type :
- Periodical
- Accession number :
- ejs43505998
- Full Text :
- https://doi.org/10.1021/acs.jnatprod.7b00527