Asymmetric synthesis of a tricyclic benzofuran motif: A privileged core structure in biologically active molecules

Research output: Contribution to journalArticle

Abstract

An efficient synthetic strategy for the asymmetric synthesis of a hexahydrodibenzofuran core structure, with a quaternary stereogenic center, emerges by employing a chiral reduction using Corey's (S)-Me-CBS-oxazaborolidine reagent followed by a Mitsunobu reaction to set the stereochemistry. A Pd-mediated intramolecular Heck reaction concludes the tricyclic core structure. Finally, a Pd/C catalyzed reduction yields the target molecule in 21% overall yield over 6 steps.

Details

Authors
External organisations
  • University of Gothenburg
  • Chemistry/medicinal Chemistry
  • ACADIA Pharmaceuticals AB
Original languageEnglish
Pages (from-to)4831-4833
Number of pages3
JournalOrganic and Biomolecular Chemistry
Volume8
Issue number21
Publication statusPublished - 2010 Nov 7
Publication categoryResearch
Peer-reviewedYes
Externally publishedYes