Synthesis of (−)-Picrotoxinin by Late-Stage Strong Bond Activation,Journal of the American Chemical Society

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Synthesis of (−)-Picrotoxinin by Late-Stage Strong Bond Activation
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-06-23 , DOI: 10.1021/jacs.0c05042
Steven W M Crossley ₁ , Guanghu Tong ₁ , Michael J Lambrecht ₁ , Hannah E Burdge ₁ , Ryan A Shenvi ₁

Affiliation

We report a concise, stereocontrolled synthesis of the neurotoxic sesquiterpenoid (-)-picrotoxinin (1, PXN). The brevity of the route is due to regio- and stereoselective formation of the [4.3.0] bicyclic core by incorporation of a symmetrizing geminal dimethyl group at C5. Dimethylation then enables selective C-O bond formation in multiple intermediates. A series of strong bond (C-C and C-H) cleavages convert the C5 gem-dimethyl group to the C15 lactone of PXN.

中文翻译：

通过后期强键激活合成 (−)-印防己毒素

我们报告了神经毒性倍半萜类化合物 (-)-印防己毒素 (1, PXN) 的简洁、立体控制合成。该路线的简洁性是由于通过在 C5 处掺入对称的偕二甲基基团来区域和立体选择性地形成[4.3.0]双环核心。二甲基化可以在多个中间体中选择性形成 CO 键。一系列强键（CC 和 CH）裂解将 C5 偕二甲基基团转化为 PXN 的 C15 内酯。

更新日期：2020-06-23

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