Flexible Total Synthesis of (±)-Aureothin, a Potent Antiproliferative Agent.
J Org Chem
; 81(12): 5190-201, 2016 06 17.
Article
em En
| MEDLINE
| ID: mdl-27213834
ABSTRACT
Amenable to late-stage preparation of analogues, a flexible and convergent total synthesis of (±)-aureothin is presented. The strategy was based on a desymmetrization of α,α'-dimethoxy-γ-pyrone by a process combining 1,4-addition and alkylation of vinylogous enolate to stereoselectively reach the backbone of the target. Palladium-catalyzed cyanation of an elaborated and isomerizable E,Z dienyl motif followed by Pinner cyclization enabled the construction of the tetrahydrofuran motif while a first approach based on a late-stage oxidation was unsuccessful.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Cromonas
/
Antifúngicos
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2016
Tipo de documento:
Article
País de afiliação:
França