MODEL STUDIES OF SYNTHESIS OF ECHITAMINE AND RELATED INDOLE ALKALOIDS .2.
MODEL STUDIES OF SYNTHESIS OF ECHITAMINE AND RELATED INDOLE ALKALOIDS .2.
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DOI：
10.1021/jo00956a032
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发表时间：
1973-01-01
影响因子：
3.6
通讯作者：
NELSON, SJ
中科院分区：
文献类型：
--
作者：
DOLBY, LJ;NELSON, SJ
描述了合成阿瓜氨胺五环骨架的尝试。这种合成方法的关键步骤是通过亲核取代反应形成C-6到C-7键。这种转化将从四氢咔唑中间体16完成阿夸胺骨架，该中间体带有所需的五个环中的四个。然而，所有试图生成关键的C-6到C-7键的尝试都失败了。报道了几个新的四环四氢咔唑衍生物的合成，以及一个意外地指向吲哚[2，3-c]降冰片-3-烯-2-酮(12)和吲哚[2，3-5]环庚烷-2，4-二烯酮(13)的序列。
Attempts to synthesize the pentacyclic skeleton of akuammiline are described. The key step in thissynthetic approach is the formation of the C-6 to C-7 bond by a nucleophilic substitution reaction. This trans-formation would complete the akuammiline skeleton from the tetrahydrocarbazole intermediate 16 which bears four of the required five rings. However, all attempts to generate the crucial C-6 to C-7 bond met with failure. The synthesis of several novel tetracyclic tetrahydrocarbazole derivatives is presented along with a sequence leading unexpectedly to indolo [2, 3-c] norcar-3-en-2-one (12) and indolo [2, 3-5] cyclohepta-2, 4-dienone (13).