Total Synthesis and Structural Reassignment of Lyngbyaloside C Highlighted by Intermolecular Ketene Esterification.
Total Synthesis and Structural Reassignment of Lyngbyaloside C Highlighted by Intermolecular Ketene Esterification.
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DOI：
10.1002/chem.201502132
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发表时间：
2015-07-20
期刊：
影响因子：
--
通讯作者：
Taylor RE
中科院分区：
文献类型：
--
作者：
Chang CF;Stefan E;Taylor RE
lynbya aloside C是一种经典的大环内酯类化合物，从lynbya bouilloni中分离出来，对几种癌细胞具有中等的抗癌活性。在这里，我们报道了柳桂苷c的首次全合成和立体构型重配。合成突出了一个分子间烯酮酯化反应，形成了关键的叔酯和四氢吡喃。此外，利用区域定向和立体定向的亲电醚转移反应，描述了一种新的、简洁的合成1,3-syn仲、叔二醇片段的途径。重新分配：已报道了聚酮天然产物lybyalside C的正常结构的总合成，并对其最初分配的立体化学进行了修正。采用高会聚策略制备了该化合物的三个非对映异构体。
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. Reassigned: The total synthesis of the nomimal structure for the polyketide natural product lybyaloside C has been reported along with a correction of its originally assigned stereochemistry. Three diasteremerisomers of the compound were prepared using a highly convergent strategy.
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