Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, China.
Org Lett. 2013 Sep 6;15(17):4402-5. doi: 10.1021/ol4019425. Epub 2013 Aug 15.
The first total synthesis of cyanthiwigins A, C, H and concise synthesis of cyanthiwigin G was achieved from a common intermediate. A modified formal [4 + 2] cycloaddition was developed to construct the key cis-hydrindanone (A-B). Stereospecific 1,4-addition, alkylation, and ring-closing metathesis were used to build the tricarbocyclic ring system (A-B-C). Various site-selective oxidations were applied to create the desired oxidation states of the different cyanthiwigins.
从一个共同的中间体实现了 cyanthiwigins A、C、H 的首次全合成和 cyanthiwigin G 的简洁合成。开发了一种改良的形式[4 + 2]环加成反应来构建关键的顺式-氢化茚酮（A-B）。立体特异性的 1,4-加成、烷基化和环 closing metathesis 用于构建三环碳环系统（A-B-C）。各种位点选择性氧化被应用于创建不同 cyanthiwigins 的所需氧化态。
