Research on Au(I)-catalyzed ene-yne cycloisomerization for construction of quassinoid scaffold

Yuta Oki, Masahisa Nakada

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

Compounds that undergo Au(I)-catalyzed cycloisomerizations affording tetracyclic products that can be converted into compounds with the skeleton of bruceantin are described. The Au(I)-catalyzed cycloisomerizations reported herein are hindered by a 1,3-diaxial interaction between the substituent and the methyl group in the transition state. The use of small substituents was found to increase the yield of the desired product, while the reaction of substrates with large substituents afford undesired constitutional isomers.

Original languageEnglish
Pages (from-to)926-929
Number of pages4
JournalTetrahedron Letters
Volume59
Issue number10
DOIs
Publication statusPublished - 2018 Mar 7

Keywords

  • Au(I)-catalysis
  • Bruceantin
  • Ene-yne cycloisomerization
  • Quassinoid
  • Stereoselective

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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