手性磷酸不对称催化合成四氢吡喃杂环化合物

Chiral Phosphate-catalysed Synthesis of Tetrahydropyran Heterocycles

四氢吡喃环结构广泛存在于天然活性物质中。四氢吡喃环类化合物及其衍生物有良好的降糖、抗菌、抗炎、抗肿瘤等药理学活性。本文以4-戊炔-1-醇为起始原料,经烷基化、Dess-Martin氧化、Witting反应、脱保护基、Diels-Alder反应等利用手性磷酸催化剂不对称催化合成含有四氢吡喃环单元的六元骈六元环化合物,并且产物有良好的对映选择性(93%ee)。

Tetrahydropyran ring structures are widely found in natural active substances.Tetrahydropyran ring compounds and their derivatives have good hypoglycemic,antibacterial,anti-inflammatory,ant i-tumour and other pharmacological activities.In this paper,4-pentyn-1-ol was used as starting material for the asymmetric catalytic synthesis of hexameric and hexameric cyclic compounds containing tetrahydropyran ring units via alkylation,Dess-Martin oxidation,Witting reaction,deprotecting groups,and Diels-Alder reaction using chiral phosphoric acid catalysts and the products showed good enantioselectivity(93%ee).