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

14 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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title = "Rapid Assembly of Protoilludane Skeleton through Tandem Catalysis: Total Synthesis of Paesslerin A and Its Structural Revision",

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.",

author = "Yuzo Mogi and Kazato Inanaga and Hidetoshi Tokuyama and Masataka Ihara and Yousuke Yamaoka and Yamada, {Ken Ichi} and Kiyosei Takasu",

note = "Funding Information: We thank JSPS KAKENHI (Grant No. 16H05073), MEXT KAKENHI (Grant Nos. JP16H01147 and JP18H04406 in Middle Molecular Strategy), and AMED Platform for Supporting Drug Discovery and Life Science Research, the Uehara Memorial Foundation, and the Hoansha Foundation. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = jun,

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doi = "10.1021/acs.orglett.9b01089",

language = "English",

volume = "21",

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journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Rapid Assembly of Protoilludane Skeleton through Tandem Catalysis

T2 - Total Synthesis of Paesslerin A and Its Structural Revision

AU - Mogi, Yuzo

AU - Inanaga, Kazato

AU - Tokuyama, Hidetoshi

AU - Ihara, Masataka

AU - Yamaoka, Yousuke

AU - Yamada, Ken Ichi

AU - Takasu, Kiyosei

N1 - Funding Information: We thank JSPS KAKENHI (Grant No. 16H05073), MEXT KAKENHI (Grant Nos. JP16H01147 and JP18H04406 in Middle Molecular Strategy), and AMED Platform for Supporting Drug Discovery and Life Science Research, the Uehara Memorial Foundation, and the Hoansha Foundation. Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/6/7

Y1 - 2019/6/7

N2 - 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.

AB - 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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JO - Organic Letters

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SN - 1523-7060

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ER -

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

Abstract

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