Stereocontrolled Semisyntheses of Elliptone and 12aß-Hydroxyelliptone.
J Nat Prod
; 80(10): 2751-2755, 2017 10 27.
Article
em En
| MEDLINE
| ID: mdl-29039664
ABSTRACT
Operationally simple, stereocontrolled semisyntheses of the anticancer rotenoids elliptone and 12aß-hydroxyelliptone, isolated from Derris elliptica and 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 12aß-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 12aß-hydroxyelliptone is also described.
Texto completo:
1
Coleções:
01-internacional
Temas:
Geral
Base de dados:
MEDLINE
Assunto principal:
Rotenona
/
Benzopiranos
/
Derris
Idioma:
En
Revista:
J Nat Prod
Ano de publicação:
2017
Tipo de documento:
Article
País de afiliação:
Reino Unido