Debenzylative Cycloetherification: An Overlooked Key Strategy for Complex Tetrahydrofuran Synthesis

Abdellatif Tikad, Julien Delbrouck, Stéphane Vincent

Research output: Contribution to journalReview article

Abstract

Tetrahydrofuran (THF) is a major structural feature found in many synthetic and natural products displaying a variety of biological properties. This review summarizes the main synthetic approaches that have been developed to construct tetrahydrofuran moieties involving debenzylative cycloetherification reactions (DBCE). Interestingly, this reaction is regio- and stereoselective without the requirement of a selective protection/deprotection strategy. Many applications of this process have been reported, including carbafuranoside synthesis, regioselective deprotection of the benzyl group positioned γ to an alkene, and total synthesis of natural products. The stereochemical outcome and the mechanism of these interesting transformations are also discussed.

Original languageEnglish
Pages (from-to)9456-9476
Number of pages21
JournalChemistry: A European Journal
Volume22
Issue number28
DOIs
Publication statusPublished - 4 Jul 2016

Keywords

  • cyclization
  • heterocycles
  • stereoselectivity
  • tetrahydrofuran
  • total synthesis

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  • Student Theses

    Development of new debenzylative cyclization reactions & de novo synthesis of difluorinated glycomimetics

    Author: Delbrouck, J., 20 Nov 2018

    Supervisor: Vincent, S. (Supervisor), Lanners, S. (President), Berionni, G. (Jury), Singleton, M. S. (External person) (Jury) & Sollogoud, M. (External person) (Jury)

    Student thesis: Doc typesDoctor of Sciences

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