多环缩醛并吡喃并[3,2-c]吡喃-5(2H)-酮衍生物的立体选择性合成。

Diastereoselective synthesis of polycyclic acetal-fused pyrano[3,2-c]pyran-5(2H)-one derivatives.

机构信息

Department of Chemistry, Seoul National University, Seoul 151-747, Korea.

出版信息

J Org Chem. 2009 Mar 6;74(5):2171-4. doi: 10.1021/jo8023889.

PMID:19193119

Abstract

A facile and efficient diastereoselective one-pot synthesis of polycyclic acetal-fused pyrano[3,2-c]pyrane-5(2H)-one was achieved through the annulation reaction of 2-C-formyl glycals with various 4-hydroxycoumarins and 4-hydroxy-6-methyl-2H-pyran-2-one. The asymmetric induction was significantly influenced by the C-4 stereogenic center of 2-C-formyl glycals. The resulting polycyclic acetal-fused pyranopyrones demonstrated anticancer activities.

摘要

通过 2-C-甲酰基糖醛与各种 4-羟基香豆素和 4-羟基-6-甲基-2H-吡喃-2-酮的环合反应，实现了多环缩醛并吡喃并[3,2-c]吡喃-5(2H)-酮的简便高效的非对映选择性一锅合成。不对称诱导受 2-C-甲酰基糖醛的 C-4 立体中心的显著影响。得到的多环缩醛并吡喃并吡喃酮具有抗癌活性。