Gonzalez-Bulnes Patricia, Casas Josefina, Delgado Antonio, Llebaria Amadeu
Research Unit on Bioactive Molecules (RUBAM), Departament de Química Orgànica Biològica, Institut d' Investigacions Químiques, i Ambientals de Barcelona (IIQAB-CSIC), Jordi Girona 18-26, 08034 Barcelona, Spain.
Carbohydr Res. 2007 Sep 3;342(12-13):1947-52. doi: 10.1016/j.carres.2007.04.024. Epub 2007 May 5.
A new synthesis of enantiomerically pure 1-amino-1-deoxy-myo-inositol is reported. The route described employs p-benzoquinone, an achiral compound, as the starting material to give conduritol B tetraacetate in three steps. Kinetic resolution of this compound using a palladium catalyst with a chiral ligand allows access to a conduritol B tetraester in high enantiomeric excess. This compound is transformed into tetrabenzyl conduritol B epoxide, which is regioselectively opened with azide to give the key azidocyclitol. Final transformation into (-)-1-amino-1-deoxy-myo-inositol hydrochloride is achieved in four synthetic steps. This sequence allows the synthesis of this compound in high enantiomeric purity in a semi-preparative scale.
报道了一种对映体纯的1-氨基-1-脱氧-肌醇的新合成方法。所描述的路线以对苯醌（一种非手性化合物）为起始原料，通过三步反应得到Conduritol B四乙酸酯。使用带有手性配体的钯催化剂对该化合物进行动力学拆分，可得到高对映体过量的Conduritol B四酯。该化合物转化为四苄基Conduritol B环氧化物，然后用叠氮化物进行区域选择性开环，得到关键的叠氮环糖醇。通过四个合成步骤最终转化为（-）-1-氨基-1-脱氧-肌醇盐酸盐。该合成路线能够以半制备规模高对映体纯度地合成该化合物。
