Expedient Synthesis of Alphitolic Acid and Its Naturally Occurring 2- O-Ester Derivatives.
J Nat Prod
; 82(4): 895-902, 2019 04 26.
Article
en En
| MEDLINE
| ID: mdl-30768265
The expedient synthesis of alphitolic acid (1) as well as its natural C-3-epimer and 2- O-ester derivatives was accomplished in a few steps from the readily commercially available betulin (9). A Rubottom oxidation delivered an α-hydroxy group in a stereo- and chemoselective manner. The diastereoselective reduction of the α-hydroxy ketone was key to accessing the 1,2-diol moiety of this class of natural products. Our concise and stereoselective synthetic protocol allowed the gram-scale synthesis of these natural products, which will facilitate future biological evaluations.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Triterpenos
/
Productos Biológicos
Idioma:
En
Revista:
J Nat Prod
Año:
2019
Tipo del documento:
Article
Pais de publicación:
Estados Unidos