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Proline‐Catalyzed Knoevenagel Condensation/[4+2] Cycloaddition Cascade Reaction: Application to Formal Synthesis of Averufin
Author(s) -
Tan Haibo,
Chen Xinzheng,
Chen Huiyu,
Liu Hongxin,
Qiu Shengxiang
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500559
Subject(s) - knoevenagel condensation , chemistry , cycloaddition , catalysis , organocatalysis , formal synthesis , proline , combinatorial chemistry , organic chemistry , cascade reaction , stereochemistry , enantioselective synthesis , amino acid , biochemistry
A remarkable proline‐catalyzed method for the construction of biologically interesting oxygen‐bridged tricyclic ketal skeletons was uncovered by starting from a variety of readily available cyclic 1,3‐diketones and either 1,4‐ or 1,5‐dicarbonyl substrates. The approach, which mimics a biosynthetic Knoevenagel condensation/[4+2] cycloaddition sequence, establishes a viable synthetic strategy for the efficient formal synthesis of averufin.