通过分子间烯酮酯化实现的林格比糖苷C的全合成及结构重新归属
Total Synthesis and Structural Reassignment of Lyngbyaloside C Highlighted by Intermolecular Ketene Esterification.
作者信息
Chang Chia-Fu, Stefan Eric, Taylor Richard E
机构信息
Warren Family Research Center for Drug Discovery and Development and the Department of Chemistry & Biochemistry, 250 Nieuwland Science Hall, University of Notre Dame, Notre Dame, IN 46556-5670 (USA).
出版信息
Chemistry. 2015 Jul 20;21(30):10681-6. doi: 10.1002/chem.201502132. Epub 2015 Jun 23.
Abstract
Lyngbyaloside C, a classic macrolide, isolated from Lyngbya bouilloni, has shown moderate anticancer activity against several cancer cell lines. Here, we report the first total synthesis and stereochemical configuration reassignment of lyngbyaloside C. The synthesis highlights a one-pot intermolecular ketene esterification reaction to form the crucial tertiary ester and tetrahydropyran. In addition, a novel and concise synthetic pathway towards the 1,3-syn secondary, tertiary diol fragment is described using a regio- and stereospecific electrophilic ether transfer reaction.
摘要
林格比糖苷C是一种从布氏林格比藻中分离出的经典大环内酯，已显示出对多种癌细胞系具有中等抗癌活性。在此，我们报道了林格比糖苷C的首次全合成及立体化学构型重新确定。该合成突出了一锅法分子间烯酮酯化反应以形成关键的叔酯和四氢吡喃。此外，还描述了一种使用区域和立体特异性亲电醚转移反应合成1,3-顺式仲、叔二醇片段的新颖且简洁的合成途径。
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