Bioinspired Divergent Synthesis of Aspersteroids A and B.
J Am Chem Soc
; 146(10): 6481-6486, 2024 03 13.
Article
en En
| MEDLINE
| ID: mdl-38421318
ABSTRACT
Aspersteroids A and B are novel ergostane-type 18,22-cyclosterols with immunosuppressive and antimicrobial activities. Herein, we report the first synthesis of these two natural products, which was accomplished in 15 and 14 steps, respectively, from commercially available ergosterol by means of a bioinspired divergent approach. Key features of this synthesis include an unprecedented radical relay cyclization that was initiated by iron(II)-mediated decomposition of an alkyl hydroperoxide to construct the E ring cyclopentane motif; a titanium(III)-mediated diastereoselective radical reduction of an epoxide to install the challenging C22 stereocenter; and highly regioselective, divergent late-stage oxidations to access the highly oxidized core framework.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Productos Biológicos
/
Compuestos Epoxi
Idioma:
En
Revista:
J Am Chem Soc
Año:
2024
Tipo del documento:
Article
País de afiliación:
China