Synthesis of trans,trans,cis-fused tetracyclic skeleton via radical domino cyclization

Miyu Furuta, Kengo Hanaya, Takeshi Sugai, Mitsuru Shoji

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Limonoids are characterized by a polycyclic structure and show a wide variety of bioactivities. In particular, mesendanin L, 12-hydroxyamoorastatone, and meliatoosenin F have unique structures containing a trans-A/B/C and cis-C/D-fused tetracyclic skeleton. We synthesized the core structure of these limonoids via Mn(OAc)3 and Cu(OAc)2-mediated radical domino cyclization of an acyclic tetraene precursor having a terminal β-keto ester. To the best of our knowledge, this is the first example of the radical-mediated construction of a 6/6/6/5-membered tetracyclic skeleton.

Original languageEnglish
Pages (from-to)2316-2322
Number of pages7
JournalTetrahedron
Volume73
Issue number16
DOIs
Publication statusPublished - 2017

Keywords

  • Domino cyclization
  • Limonoid
  • Radical cyclization
  • Stereoselective
  • Tetracyclic core

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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