The Role of N-Substitution in Regio- and Stereoselective Vinylogous Imidonaphthoquinone (VINAquinone) [2 + 2] Photocycloadditions.
Org Lett
; 26(23): 4921-4925, 2024 Jun 14.
Article
en En
| MEDLINE
| ID: mdl-38814707
ABSTRACT
Described in this manuscript are intramolecular [2 + 2] photocycloadditions of readily available vinylogous imidonaphthoquinones whose regio- and diastereoselectivity is dependent on the substitution on the vinylogous imide. When exposed to 419 nm light, 2° vinylogous imidonaphthoquinones give novel bridged tetracyclic aza-anthraquinones from a rare crossed [2 + 2] cycloaddition reaction. In contrast, exposure of the corresponding 3° substrates to white light leads to linear adducts. Also outlined here are auxiliary controlled diastereoselective reactions and cyclobutane fragmentations as a means of generating the spirofused γ-lactam moiety present in the ansalactam family of natural product.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Org Lett
Asunto de la revista:
BIOQUIMICA
Año:
2024
Tipo del documento:
Article
País de afiliación:
Estados Unidos
Pais de publicación:
Estados Unidos