A Unified Strategy for the Enantiospecific Total Synthesis of Delavatine A and Formal Synthesis of Incarviatone A
A Unified Strategy for the Enantiospecific Total Synthesis of Delavatine A and Formal Synthesis of Incarviatone A
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DOI：
10.1021/jacs.9b07693
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发表时间：
2019-09-11
影响因子：
15
通讯作者：
Sarpong, Richmond
中科院分区：
文献类型：
--
作者：
Palani, Vignesh;Hugelshofer, Cedric L.;Sarpong, Richmond
我们描述了一种对称启发的合成方法，使delavatine a的短合成和incarviatone a的正式合成成为可能，这是两种生物合成相关的天然产物。这些天然产物的吲哚核心是通过级联序列构建的，涉及在单个锅中发生的五种转化。利用对称性，我们可以将这两种天然产物追溯到一个多功能构建块，3,5-二溴-2-吡咯酮，并描述了与该多卤化杂环的位点选择性交叉偶联相关的研究。此外，我们的策略还提供了一种假定的生物遗传前体，试图从该前体合成两种天然产物。
We describe a symmetry-inspired synthetic approach that has enabled a short synthesis of delavatine A and a formal synthesis of incarviatone A, which are two likely biosynthetically related natural products. The indane core of these natural products was constructed through a cascade sequence involving five transformations that occur in a single pot. Leveraging symmetry has allowed us to trace both natural products back to a versatile building block, 3,5-dibromo-2-pyrone, and studies related to site-selective cross-coupling of this polyhalogenated heterocycle are described. In addition, our strategy gave access to a putative biogenetic precursor, from which the syntheses of both natural products were attempted.