Total syntheses of spiroviolene and spirograterpene A: a structural reassignment with biosynthetic implications,Chemical Science

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Total syntheses of spiroviolene and spirograterpene A: a structural reassignment with biosynthetic implications
Chemical Science ( IF 7.6 ) Pub Date : 2020-09-30 , DOI: 10.1039/d0sc04686h
Hyung Min Chi ₁ , Charles J F Cole ₁ , Pengfei Hu ₁ , Cooper A Taylor ₁ , Scott A Snyder ₁

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The recent natural product isolates spiroviolene and spirograterpene A are two relatively non-functionalized linear triquinane terpenes with a large number of structural homologies. Nevertheless, three significant areas of structural disparity exist based on their original assignments, one of which implies a key stereochemical divergence early in their respective biosyntheses. Herein, using two known bicyclic ketone intermediates, a core Pd-catalyzed Heck cyclization sequence, and several chemoselective transformations, we describe concise total syntheses of both natural product targets and propose that the structure of spiroviolene should be reassigned. As a result, these natural products possess greater homology than previously anticipated.

中文翻译：

螺紫烯和螺环烯 A 的全合成：具有生物合成意义的结构重新分配

最近分离出来的天然产物螺紫烯和螺环萜烯A是两种相对非功能化的线性三奎烷萜烯，具有大量的结构同源性。然而，根据它们最初的分配，存在三个显着的结构差异领域，其中之一意味着它们各自的生物合成早期存在关键的立体化学分歧。在此，使用两种已知的双环酮中间体、核心 Pd 催化的 Heck 环化序列和几种化学选择性转化，我们描述了两种天然产物目标的简明全合成，并提出应重新分配螺紫烯的结构。因此，这些天然产物具有比之前预期更高的同源性。

更新日期：2020-10-14

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