An aza-Robinson Annulation Strategy for the Synthesis of Fused Bicyclic Amides: Synthesis of (±)-Coniceine and Quinolizidine.
Org Lett
; 25(43): 7940-7945, 2023 Nov 03.
Article
en En
| MEDLINE
| ID: mdl-37877616
ABSTRACT
An aza-Robinson annulation strategy is described using a NaOEt-catalyzed conjugate addition of cyclic imides onto vinyl ketones, followed by a TfOH-mediated intramolecular aldol condensation to afford densely functionalized fused bicyclic amides. The potential use of these amides in the synthesis of alkaloids is demonstrated by the sequential conversion of appropriate precursors to (±)-coniceine and quinolizidine in two additional steps, thus allowing their preparation in overall 40 and 44% yields, respectively.
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Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Org Lett
Asunto de la revista:
BIOQUIMICA
Año:
2023
Tipo del documento:
Article
País de afiliación:
Colombia