Rapid Assembly of Protoilludane Skeleton through Tandem Catalysis: Total Synthesis of Paesslerin A and Its Structural Revision

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 achi...

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Published inOrganic letters Vol. 21; no. 11; pp. 3954 - 3958
Main Authors Mogi, Yuzo, Inanaga, Kazato, Tokuyama, Hidetoshi, Ihara, Masataka, Yamaoka, Yousuke, Yamada, Ken-ichi, Takasu, Kiyosei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.06.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLIZATIONS
CYCLOADDITIONS
STRATEGY
SILYL ENOL ETHERS
ISOMERIZATION
CHEMISTRY
ILLUDOL
SUBSTANCES
IMIDE
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Summary: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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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01089