Development and Utilization of Versatile Chirl Building Blocks

在本研究中，采用酶或化学动力学拆分方法，开发了三种具有凸面选择性的versatole手性构件。所有构建块都具有一个烯酮和一个掩膜烯酮基团，由于其固有的立体化学性质，允许非对映控制修饰。这些手性分子作为手性构建块的多功能性被证明是通过对映和非对映控制构建的多种生理活性天然产物，在本研究中合成了前列腺素（关键中间体），(-)-吗啡，(+)-tanikolide,(-)-马来内酯，(-)-kainic acid, (+)-febrifugine,(+)-和(-)-左旋葡萄糖酮，(-)-shikimic acid, (-)-semburine, (-)-antirhine,(-)-奎宁（关键中间体），(+)-uleine,(-)-马马霉素，（+）-arnicenone, (-)- physostamine, (-)-physovenine, (-)-aphanorphine, (-)-iridolactone, (+)-pedicularis-lactone, simplactone A, (-)-tetrahydrolipstatin， 8个醛己糖，6个conduritols，假单胞酸，铁二醇，(+)- 20r -dihydrocleavamine, (-)- qubrachamine, (-)-menisdaurilide, (-)-mesembrine，和(+)- seletinum A。

During the present investigation, three versatole chiral building blocks exhibiting convex-face selectivity have been developed by employing either enzymatic or chemical kinetic resolution method. All building blocks possess an enone and a masked enone moieties which allowed diastereocontrolled modification owing to their inherent stereochemical nature. Versatility of these chiral molecules as chiral building blocks were demonstrated by enantio- and diastereocontrolled construction of a variety of physiologically active natural products synthesized in the present investigation are prostaglandins (key intermediate), (-)-morphine, (+)-tanikolide, (-)-malyngolide, (-)-kainic acid, (+)-febrifugine, (+)- and (-)-levoglucosenone, (-)-shikimic acid, (-)-semburine, (-)-antirhine, (-)-quinine (key intermediate), (+)-uleine, (-)-aristeromycin, (+)-arnicenone, (-)-physostigmine, (-)-physovenine, (-)-aphanorphine, (-)-iridolactone, (+)-pedicularis-lactone, simplactone A, (-)-tetrahydrolipstatin, eight aldohexoses, six conduritols, pseudomonic acids, ferruginol, (+)-20R-dihydrocleavamine, (-)-quebrachamine, (-)-menisdaurilide, (-)-mesembrine, and (+)-sceletinum A.