10-Step Asymmetric Total Synthesis and Stereochemical Elucidation of (+)-Dragmacidin D.
10-Step Asymmetric Total Synthesis and Stereochemical Elucidation of (+)-Dragmacidin D.
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DOI：
10.1002/anie.201504113
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发表时间：
2015-08-17
期刊：
影响因子：
--
通讯作者：
Zakarian A
中科院分区：
文献类型：
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作者：
Jackson JJ;Kobayashi H;Steffens SD;Zakarian A
通过10步反应完成了dragmacidin D（1）的不对称合成。其唯一的立构中心是使用C2-对称四胺和N-（三甲基甲硅烷基）-叔丁基氨基锂作为烯醇化试剂实现的直接不对称烷基化来设置的。在杂环亚基的会聚组装中采用中心Larock吲哚合成。这项工作的立体化学证据强烈支持预测的6′″位S构型，与天然产物dragmacidin家族的其他成员一致。
The asymmetric synthesis of dragmacidin D (1) has been completed in 10 steps. Its sole stereocenter was set using direct asymmetric alkylation enabled by a C2-symmetric tetramine and lithium N-(trimethylsilyl)-tert-butylamide as the enolization reagent. A central Larock indole synthesis was employed in a convergent assembly of heterocyclic subunits. The stereochemical evidence from this work strongly supports the predicted S configuration at 6′″ position consistent with other members of the dragmacidin family of natural products.