Direct Entry to Erythronolides via a Cyclic Bis[Allene]
Direct Entry to Erythronolides via a Cyclic Bis[Allene]
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DOI：
10.1021/ja207496p
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发表时间：
2011-09-28
影响因子：
15
通讯作者：
Williams, Lawrence J.
中科院分区：
文献类型：
--
作者：
Liu, Kai;Kim, Hiyun;Williams, Lawrence J.
抗生素大环内酯类的复杂性和低易处理性对通过半合成或全合成解决耐药性问题提出了严峻的挑战。在这里，我们描述了一种新的策略，涉及到一个复杂的，但听话的大环化合物的制备和这种大环化合物转化成一系列的β-ronectin同系物。这些化合物代表了类红霉素结构空间的有价值的部分，并构成了具有在该空间中提供进一步购买的潜力的中间体。路线很短。从大环化合物中以三个或更少的步骤制备藜芦内酯，大环化合物以11个步骤的最长线性顺序制备。
The complexity and low tractability of antibiotic macrolides pose serious challenges to addressing the problem of resistance through semi- or total synthesis. Here we describe a new strategy involving the preparation of a complex yet tractable macrocycle and the transformation of this macrocycle into a range of erythronolide congeners. These compounds represent valuable sectors of erythromycinoid structure space and constitute intermediates with the potential to provide further purchase in this space. The routes are short. The erythronolides were prepared in three or fewer steps from the macrocycle, which was prepared in a longest linear sequence of 11 steps.