Total Synthesis of Actinophyllic Acid.
Angew Chem Int Ed Engl
; 56(40): 12277-12281, 2017 09 25.
Article
em En
| MEDLINE
| ID: mdl-28836325
ABSTRACT
Herein we report a total synthesis of the indolohydroazocine natural product actinophyllic acid. The target molecule was retrosynthetically deconvoluted to render a greatly simplified and symmetrical [4.4.1] bicyclic trienone, the desymmetrization of which was carefully examined under a variety of conditions, including oxidative, reductive, and transition-metal-catalyzed transformations. Ultimately, the successful synthetic strategy featured chemoselective catalytic dihydroxylation, desymmetrizing nitrile oxide dipolar cycloaddition, and palladium-catalyzed aminoarylation to sequentially modify the three olefins within the trienone, followed by a late-stage reductive cascade indolization and alkylation to complete the target molecule.
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1
Bases de dados:
MEDLINE
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Ano de publicação:
2017
Tipo de documento:
Article
País de afiliação:
Coréia do Sul