化学
苦参碱
天然产物
全合成
分子内力
立体化学
非对映体
共价键
共轭体系
分子内反应
组合化学
有机化学
色谱法
聚合物
作者
Nicholas L. Magann,Erin Westley,Madison J. Sowden,Michael G. Gardiner,Michael S. Sherburn
摘要
The total synthesis of three diastereomeric matrine natural products is reported. The 8-step synthesis commences with simple acyclic precursors, forms all 4 rings of the tetracyclic natural product framework, and forges 10 of the 20 covalent bonds of the target structure. A cross-conjugated triene is positioned at the core of an acyclic branched structure. This precursor collapses to the tetracyclic natural product framework through an orchestrated sequence of two separate intramolecular cycloadditions. A subsequent, late-stage hydrogenation is accompanied by strain-release redox epimerizations to deliver the three natural products. An unprecedented carba-analogue is prepared in the same way. Semisynthetic manipulations of matrine provide access to 10 additional natural products.
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