Synthesis of (−)-Picrotoxinin by Late-Stage Strong Bond Activation
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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.
创建时间：
2020-06-23
