Proline‐Catalyzed Knoevenagel Condensation/[4+2] Cycloaddition Cascade Reaction: Application to Formal Synthesis of Averufin | Zendy

Tan Haibo | Zendy; Chen Xinzheng | Zendy; Chen Huiyu | Zendy; Liu Hongxin | Zendy; Qiu Shengxiang | Zendy

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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.

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