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钯催化的正交 Knoevenagel/Perkin 缩合-脱羧-Heck/Suzuki 序列:苯甲醛转化为羟基官能化抗糖尿病二苯乙烯肉桂酰杂合体和不对称二苯乙烯的串联转化。

Pd-catalyzed orthogonal Knoevenagel/Perkin condensation-decarboxylation-Heck/Suzuki sequences: tandem transformations of benzaldehydes into hydroxy-functionalized antidiabetic stilbene-cinnamoyl hybrids and asymmetric distyrylbenzenes.

机构信息

Natural Plant Products Division, Council of Scientific and Industrial Research, Institute of Himalayan Bioresource Technology (I.H.B.T.), Palampur (H.P.) 176061, India.

出版信息

Chemistry. 2011 Sep 5;17(37):10350-6. doi: 10.1002/chem.201101174. Epub 2011 Aug 2.

DOI:10.1002/chem.201101174
PMID:21812043
Abstract

Tandem reactions that involve chemoselective Knoevenagel/Perkin condensation-decarboxylation-Heck/Suzuki coupling or Heck-aldol sequences have been achieved. This enabled the first concise and efficient synthesis of several important hydroxy-functionalized compound classes, such as stilbene-cinnamoyl hybrids (potent protein tyrosine phosphatase1B inhibitors), cinnamoyl-cinnamic acid hybrids, asymmetric distyrylbenzenes, and biarylstyrenes. Previously reported synthesis require multiple steps and protection/deprotection manipulations.

摘要

串联反应涉及化学选择性 Knoevenagel/Perkin 缩合-脱羧-Heck/Suzuki 偶联或 Heck-aldol 序列已被实现。这使得几种重要的羟基官能化化合物类别的首次简洁高效的合成成为可能,如二苯乙烯-肉桂酰杂合(强效蛋白酪氨酸磷酸酶 1B 抑制剂)、肉桂酰-肉桂酸杂合、不对称二苯乙烯和联苯乙烯。以前报道的合成方法需要多步反应和保护/脱保护操作。

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