Total Synthesis of Atrachinenins A and B.
J Am Chem Soc
; 144(50): 22844-22849, 2022 12 21.
Article
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| MEDLINE
| ID: mdl-36508174
ABSTRACT
Inspired by a new biosynthetic hypothesis, we report a biomimetic total synthesis of atrachinenins A and B that explains their racemic nature. The synthesis exploits an intermolecular Diels-Alder reaction between a quinone meroterpenoid and E-ß-ocimene, followed by intramolecular (3 + 2) cycloaddition and a late-stage aerobic oxidation. Divergent transformations of a simple model system gave several complex polycyclic scaffolds, while also suggesting a structure revision for atrachinenin C.
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Banco de datos:
MEDLINE
Asunto principal:
Quinonas
/
Biomimética
Idioma:
En
Año:
2022
Tipo del documento:
Article