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

Research output: Contribution to journalArticlepeer-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 languageEnglish
Pages (from-to)3954-3958
Number of pages5
JournalOrganic letters
Volume21
Issue number11
DOIs
Publication statusPublished - 2019 Jun 7

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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