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New Synthetic Approach for the Construction of Multisubstituted 2‐Acyl Furans by the IBX‐Mediated Cascade Oxidation/Cyclization of cis ‐2‐En‐4‐yn‐1‐ols (IBX=2‐Iodoxybenzoic Acid)
Author(s) -
Du Xiangwei,
Chen Haoyi,
Liu Yuanhong
Publication year - 2008
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.200801561
Subject(s) - cascade , scheme (mathematics) , organic chemistry , chemistry , combinatorial chemistry , dimethyl sulfoxide , computer science , mathematics , mathematical analysis , chromatography
Cascading reactions : A new synthetic approach for the construction of multisubstituted 2‐acyl furans with high diversity through IBX‐mediated (IBX=2‐iodoxybenzoic acid) cascade oxidation/cyclization of cis ‐2‐en‐4‐yn‐1‐ols in dimethyl sulfoxide has been developed (see scheme). A mechanistic proposal involving IBX‐promoted 5‐ exo ‐dig cyclization of an enynone intermediate is presented.