Development of an enantiodivergent strategy for the total synthesis of (+)- and (-)-dragmacidin F from a single enantiomer of quinic acid
Development of an enantiodivergent strategy for the total synthesis of (+)- and (-)-dragmacidin F from a single enantiomer of quinic acid
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DOI：
10.1021/ja050586v
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发表时间：
2005-04-27
影响因子：
15
通讯作者：
Stoltz, BM
中科院分区：
文献类型：
--
作者：
Garg, NK;Caspi, DD;Stoltz, BM
从奎尼酸的单一对映体开始，开发并成功实施了全化学合成（+）-和（-）-dragmacidin F的对映体分散策略。虽然独特的，这些对映体的合成路线共享一些关键特征，包括新的还原异构化反应，钯（II）介导的氧化碳环化反应，卤素选择性铃木耦合，和高产后期Neber重排。
An enantiodivergent strategy for the total chemical synthesis of both (+)- and (-)-dragmacidin F beginning from a single enantiomer of quinic acid has been developed and successfully implemented. Although unique, the synthetic routes to these antipodes share a number of key features, including novel reductive isomerization reactions, Pd(II)-mediated oxidative carbocyclization reactions, halogen-selective Suzuki couplings, and high-yielding late-stage Neber rearrangements.