Taming Shapeshifting Anions: Total Synthesis of Ocellatusone C,Journal of the American Chemical Society

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Taming Shapeshifting Anions: Total Synthesis of Ocellatusone C
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2022-04-14 , DOI: 10.1021/jacs.2c02627
Andre Sanchez ₁ , Thomas J Maimone ₁

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Guided by a synthetic design aimed at late-stage diversification, we report the preparation of unusual shapeshifting anions and their subsequent application to the total synthesis of the polyketide natural product ocellatusone C. Site-selective core functionalization of a readily accessible bicyclo[3.3.1]nonane architecture sets the stage for shape-selective side chain installation via a nonfluxional π-allyl Pd-complex derived from a barbaralyl-type anion. Several interesting chemical findings, including substituent-dependent bridged bicycloisomerism and the isolation of a stabilized, 3° carbon-bound Pd-ketone enolate complex, are reported.

中文翻译：

驯服变形阴离子：Ocellatusone C 的全合成

在旨在后期多样化的合成设计的指导下，我们报告了不寻常的变形阴离子的制备及其随后在聚酮化合物天然产物 ocellatusone C 的全合成中的应用。易于获得的双环的位点选择性核心功能化[3.3.1 ]壬烷结构通过衍生自巴巴拉基型阴离子的非流动 π-烯丙基 Pd 络合物为形状选择性侧链安装奠定了基础。报道了一些有趣的化学发现，包括依赖于取代基的桥接双环异构现象和稳定的 3° 碳结合的 Pd-酮烯醇络合物的分离。

更新日期：2022-04-14

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