Stereocontrolled Total Syntheses of Optically Active Furofuran Lignans

Stereocontrolled Total Syntheses of Optically Active Furofuran Lignans
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光学活性呋喃呋喃木脂素的立体控制全合成

DOI:
10.1055/s-0034-1378812
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发表时间:
2015
期刊:
Synthesis
影响因子:
--
通讯作者:
T. Kan
T. Kan
中科院分区:
--
文献类型:
--
作者:
M. Inai;R. Ishikawa;N. Yoshida;N. Shirakawa;Y. Akao;Y. Kawabe;T. Asakawa;M. Egi;Y. Hamashima;T. Kan

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通过l-脯氨酸催化双功能脲加速交叉醛反应,以高度立体控制的方式合成了植物产物(+)-芝麻素、(+)-芝麻醇、(+)-甲基胡椒醇、(+)-aschantin和(+)-5'-羟甲基胡椒醇,然后通过喹二胺中间体仿生构建了呋喃木脂素骨架。
Plant products (+)-sesamin, (+)-sesaminol, (+)-methylpiperitol, (+)-aschantin, and (+)-5'-hydroxymethylpiperitol were synthesized in a highly stereocontrolled manner throughl-proline-catalyzed bifunctional-urea-accelerated cross-aldol reaction, followed by biomimetic construction of the furofuran lignan skeleton through a quinomethide intermediate.