Hexadehydro-Diels-Alder (HDDA)-Enabled Carbazolyne Chemistry: Single Step, de Novo Construction of the Pyranocarbazole Core of Alkaloids of the Murraya koenigii (Curry Tree) Family.
Hexadehydro-Diels-Alder (HDDA)-Enabled Carbazolyne Chemistry: Single Step, de Novo Construction of the Pyranocarbazole Core of Alkaloids of the Murraya koenigii (Curry Tree) Family.
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DOI：
10.1021/jacs.6b09628
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发表时间：
2016-10-26
影响因子：
15
通讯作者：
Hoye TR
中科院分区：
文献类型：
--
作者：
Wang T;Hoye TR
本文报道了利用六氢Diels-Alder(HDDA)反应在稠合多环杂芳咔唑(即[2，3]-苯并吲哚)骨架中从头构筑苯环。该策略允许产生高度取代的苯类化合物。我们还描述了天然产物马哈尼滨和柯尼定的HDDA使能化学合成。通过形式[2+2]环加成、4个π-电环开环和6个π-电环关闭事件，用共轭烯醛捕获中间体咔唑，构成了一种生产吡喃并咪唑的可靠方法。
Here we report the use of the hexadehydro-Diels–Alder (HDDA) reaction for the de novo construction of a benzenoid ring in fused polycyclic heteroaromatic carbazole (i.e., [2,3]-benzoindole) skeletons. The strategy allows creation of highly substituted benzenoids. We also describe the HDDA-enabled chemical synthesis of the natural product alkaloids mahanimbine and koenidine. Trapping of the intermediate carbazolyne with a conjugated enal–proceeding through formal [2+2] cycloaddition, 4π-electrocyclic ring-opening, and 6π-electrocyclic ring-closing events—constitutes a robust method for producing pyranocarbazoles.