Debenzylative Cycloetherification: An Overlooked Key Strategy for Complex Tetrahydrofuran Synthesis.
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.
University of Namur (UNamur), Département de Chimie, Laboratoire de Chimie Bio-Organique, rue de Bruxelles 61, 5000, Namur, Belgium. abdel.tikad@gmail.com.
Abdellatif
A
Tikad
University of Namur (UNamur), Département de Chimie, Laboratoire de Chimie Bio-Organique, rue de Bruxelles 61, 5000, Namur, Belgium.
Julien A
JA
Delbrouck
University of Namur (UNamur), Département de Chimie, Laboratoire de Chimie Bio-Organique, rue de Bruxelles 61, 5000, Namur, Belgium. stephane.vincent@unamur.be.
Stéphane P
http://orcid.org/0000-0001-6258-9058
SP
Vincent
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D001688:Biological Products; D005663:Furans; C018674:tetrahydrofuran
cyclization; heterocycles; stereoselectivity; tetrahydrofuran; total synthesis