Rapid Assembly of Protoilludane Skeleton through Tandem Catalysis: Total Synthesis of Paesslerin A and Its Structural Revision.
Org Lett
; 21(11): 3954-3958, 2019 06 07.
Article
em En
| MEDLINE
| ID: mdl-31117698
ABSTRACT
A multicomponent domino reaction involving three mechanistically distinct Tf2NH-catalyzed reactions was developed. The reaction cascade enables the assembly of a skewed 5/6/4 tricyclic motif with migration of the reactive site with the assistance of a catalyst. The tricyclic product was used to achieve the first total synthesis of cytotoxic paesslerin A by regioselective C-H insertion of the sulfonyl carbenoid and base-promoted olefin isomerization. Our results led to the revision of the originally proposed tricyclic structure of paesslerin A.
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01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2019
Tipo de documento:
Article