Enantioselective total synthesis of (-)-FR182877

Natsumi Tanaka Suzuki, Takahiro Suzuki, Takehiko Matsumura, Yousuke Hosoya, Tomoyuki Nakazato, Masahisa Nakada

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

An enantioselective total syntfiesis of (-)-FR182877 is described. This total synthesis features 1) the one-pot stereoselective tandem IMDA-IMHDA reaction which affords the tetracyclic compound including the ABCD ring system of (-)-FR182877 with the correct new seven stereogenie centers, 2) the palladium-mediated 7-exo-trig intramolecular Heck reaction for the construction of the highly strained seven-membefed F-ring, and 3) the iridium-mediated isomerization of the allylic alcohol to the a-methyl ketone followed by epimerization and the stereoselective reduction to furnish all the stereogenic centers of (-)-FR182877.

Original languageEnglish
Pages (from-to)646-660
Number of pages15
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume69
Issue number6
DOIs
Publication statusPublished - 2011 Jun 1

Keywords

  • Anti-tumor cell compound
  • Enantioselective total synthesis
  • Intramolecular Heck reaction
  • Intramolecular diels-alder (IMDA) reaction
  • Intramolecular hetero diels-alder (IMHDA) reaction
  • Isomerisation reaction
  • Strained compound
  • Tandem IMDA-IMHDA reaction

ASJC Scopus subject areas

  • Organic Chemistry

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