Stockton Kieran P, Greatrex Ben W
School of Science and Technology, University of New England, Armidale, NSW, Australia2351.
Org Biomol Chem. 2016 Aug 21;14(31):7520-8. doi: 10.1039/c6ob00933f. Epub 2016 Jul 18.
The biorenewable chiral synthon (-)-levoglucosenone has been converted to enantiopure cyclopropyl esters using the base-promoted carbocyclisation of 4,5-epoxyvalerates. This protocol was applied to the enantiospecific synthesis of the GABAc receptor agonist (1R,2R)-trans-2-aminomethylcyclopropanecarboxylic acid ((-)-TAMP) and its enantiomer. The process was also extended to generate 1,1,2- and 1,2,3-trisubstituted cyclopropanes resulting in a formal synthesis of the selective glutamate receptor antagonist PCCG-4.
生物可再生手性合成子（-）-左旋葡萄糖酮已通过4,5-环氧戊酸酯的碱促进碳环化反应转化为对映体纯的环丙基酯。该方案应用于GABAc受体激动剂（1R,2R）-反式-2-氨基甲基环丙烷羧酸（（-）-TAMP）及其对映体的对映选择性合成。该方法还扩展到生成1,1,2-和1,2,3-三取代环丙烷，从而实现了选择性谷氨酸受体拮抗剂PCCG-4的形式合成。
