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

Yuzo Mogi; Kazato Inanaga; Hidetoshi Tokuyama; Masataka Ihara; Yousuke Yamaoka; Ken Ichi Yamada; Kiyosei Takasu

doi:10.1021/acs.orglett.9b01089

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

Yuzo Mogi, Kazato Inanaga, Hidetoshi Tokuyama, Masataka Ihara, Yousuke Yamaoka, Ken Ichi Yamada, Kiyosei Takasu

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3954-3958
Number of pages	5
Journal	Organic letters
Volume	21
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.9b01089
Publication status	Published - 2019 Jun 7

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Rapid Assembly of Protoilludane Skeleton through Tandem Catalysis : Total Synthesis of Paesslerin A and Its Structural Revision. / Mogi, Yuzo; Inanaga, Kazato; Tokuyama, Hidetoshi; Ihara, Masataka; Yamaoka, Yousuke; Yamada, Ken Ichi; Takasu, Kiyosei.

In: Organic letters, Vol. 21, No. 11, 07.06.2019, p. 3954-3958.

Research output: Contribution to journal › Article › peer-review

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