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Entry to Heterocycles Based on Indium‐Catalyzed Conia‐Ene Reactions: Asymmetric Synthesis of (−)‐Salinosporamide A
Author(s) -
Takahashi Keisuske,
Midori Michiko,
Kawano Kei,
Ishihara Jun,
Hatakeyama Susumi
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200801967
Subject(s) - catalysis , indium , ene reaction , chemistry , oxygen , nitrogen , combinatorial chemistry , medicinal chemistry , organic chemistry
Conica can : The In(OTf) 3 ‐catalyzed cyclization of nitrogen‐ and oxygen‐tethered acetylenic malonic esters gives five‐ to seven‐membered heterocycles in moderate to excellent yields (see scheme; Tf=trifluoromethanesulfonyl). The asymmetric synthesis of (−)‐salinosporamide A illustrates the synthetic utility of the method.
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