Research on Liebeskind-Srogl coupling/intramolecular Diels-Alder reaction cascade

Tomohiro Fujii, Yuta Oki, Masahisa Nakada*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

The Liebeskind-Srogl coupling/intramolecular Diels-Alder (IMDA) reaction cascade that stereoselectively affords a tricarbocyclic compound with a trans–trans-cis fused ring system including an all-carbon quaternary stereogenic center at the ring junction is described. The cascade reactions proceed quickly and stereoselectively afford the products within 2 h at room temperature in the presence of a suitable thioester. The developed protocol as well as the prepared chiral compounds are useful for the enantioselective total synthesis of terpenoids with the trans–trans-cis fused ring system.

Original languageEnglish
Pages (from-to)882-886
Number of pages5
JournalTetrahedron Letters
Volume59
Issue number10
DOIs
Publication statusPublished - 2018 Mar 7

Keywords

  • Cascade
  • Diels-Alder
  • Intramolecular
  • Liebeskind-Srogl
  • Stereoselective

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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