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Debenzylative Cycloetherification: An Overlooked Key Strategy for Complex Tetrahydrofuran Synthesis
Author(s) -
Tikad Abdellatif,
Delbrouck Julien A.,
Vincent Stéphane P.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600655
Subject(s) - tetrahydrofuran , regioselectivity , alkene , stereoselectivity , chemistry , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , solvent
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.