A highly stereoselective intramolecular Diels-Alder reaction for construction of the AB ring moiety of bruceantin

Kenji Usui, Takahiro Suzuki, Masahisa Nakada

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A highly stereoselective intramolecular Diels-Alder (IMDA) reaction for the construction of the AB ring moiety of bruceantin is described. The product of the IMDA reaction comprises a trans-AB ring junction and stereotetrad including an all carbon quaternary stereogenic center, wherein three stereogenic centers correspond to those of bruceantin. Functional groups embedded in the product are suitable for a variety of transformations. Hence, this IMDA product could be a useful intermediate for the enantioselective total synthesis of not only bruceantin, but also other bioactive compounds.

Original languageEnglish
Pages (from-to)1247-1251
Number of pages5
JournalTetrahedron Letters
Volume56
Issue number10
DOIs
Publication statusPublished - 2015 Mar 4

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Keywords

  • Diels-Alder reaction
  • Intramolecular
  • Natural product
  • Stereoselective
  • Synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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