Debenzylative Cycloetherification: An Overlooked Key Strategy for Complex Tetrahydrofuran Synthesis

Abdellatif Tikad, Julien Delbrouck, Stéphane Vincent

Résultats de recherche: Contribution à un journal/une revueArticle de revueRevue par des pairs


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.

langue originaleAnglais
Pages (de - à)9456-9476
Nombre de pages21
journalChemistry: A European Journal
Numéro de publication28
Les DOIs
Etat de la publicationPublié - 4 juil. 2016

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