(−)-Quinic acid was used as a starting material in the hemisynthesis of two epimeric carbasugars isolated from Streptomyces lincolnensis. Previous 10–12 steps syntheses for the carbasugars have been herein shortened to 4–6 steps by using quinic acid as a chiron, based on a regioselective reduction step, with stereoinversion of a tertiary center. Both C-5 epimers of (1R, 2R, 3R)-5-(hydroxymethyl)cyclohexane-1,2,3-triol were obtained in up to 76% overall yield.

中文翻译：

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从林肯链霉菌分离出的Carcarbugars的简明合成

（-）-亚奎宁酸用作从林肯链霉菌分离的两个差向异构碳节糖的半合成的起始原料。在基于区域选择性还原步骤的基础上，通过使用奎宁酸作为螯合物，三级立体立体反转，以前的10–12步的合成方法被缩短为4–6步。获得了（1 R，2 R，3 R）-5-（羟甲基）环己烷-1,2,3-三醇的两个C-5差向异构体，总产率高达76％。