Debenzylative Cycloetherification: An Overlooked Key Strategy for Complex Tetrahydrofuran Synthesis

Résultats de recherche: Contribution à un journal/une revueArticle de revue

Résumé

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
Volume22
Numéro de publication28
Les DOIs
étatPublié - 4 juil. 2016

Empreinte digitale

Biological Products
Alkenes
Olefins
tetrahydrofuran

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title = "Debenzylative Cycloetherification: An Overlooked Key Strategy for Complex Tetrahydrofuran Synthesis",
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.",
keywords = "cyclization, heterocycles, stereoselectivity, tetrahydrofuran, total synthesis",
author = "Abdellatif Tikad and Julien Delbrouck and St{\'e}phane Vincent",
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Debenzylative Cycloetherification : An Overlooked Key Strategy for Complex Tetrahydrofuran Synthesis. / Tikad, Abdellatif; Delbrouck, Julien; Vincent, Stéphane.

Dans: Chemistry: A European Journal, Vol 22, Numéro 28, 04.07.2016, p. 9456-9476.

Résultats de recherche: Contribution à un journal/une revueArticle de revue

TY - JOUR

T1 - Debenzylative Cycloetherification

T2 - An Overlooked Key Strategy for Complex Tetrahydrofuran Synthesis

AU - Tikad, Abdellatif

AU - Delbrouck, Julien

AU - Vincent, Stéphane

PY - 2016/7/4

Y1 - 2016/7/4

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AB - 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.

KW - cyclization

KW - heterocycles

KW - stereoselectivity

KW - tetrahydrofuran

KW - total synthesis

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