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Home » Methodology » Total synthesis of (–)-tubingensin B enabled by the strategic use of an aryne cyclization

Total synthesis of (–)-tubingensin B enabled by the strategic use of an aryne cyclization

Nat. Chem. 2017, 9, 944, DOI: 10.1038/nchem.2801 full text link

文献汇报人:张昕平

汇报日期: 2019119

图文摘要:


 

  • 推荐原因:

Tubingensin B的结构看似简单,但两个相邻的C(sp2)-C(sp3)键以及与咔唑相连的两个季碳手性中心都是合成的难点,更为挑战的是与咔唑稠合的双环-[3.2.2]-壬烷和高度官能化的六元环部分。该天然产物共含有5个手性中心,其中3个是季碳中心,而且有2个季碳中心还相邻。作者通过芳炔环化策略作为关键步对Tubingensin B进行了高效的全合成。这种利用芳炔环化策略构建多种复杂结构(例如构建相邻的季碳手性中心)的思路,值得深入学习研究。


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