Nature2014-06-09 4:54 PM

新型含氮天然产物被合成  Total synthesis and isolation of citrinalin and cyclopiamine congeners 

论文摘要

这篇论文报告了天然产物citrinalin B 和cyclopiamine B的首次合成。作为这项研究的一个“副产品”,作者还提出了对citrinalin B的最初结构的一个修正。氮原子在一个目标分子中的存在因氮的碱性和易于被氧化的特性而会使其合成复杂化。这个问题可以通过能够降低碱性的官能团的选择性引入和去除来绕过。异戊烯基化吲哚类生物碱citrinalin B 和 cyclopiamine B是通过对该方法的一个优化生成的,这一结果向包括奎宁和吗啡等治疗性药物在内的一类化合物打开了合成化学的大门。

Abstract 

Many natural products that contain basic nitrogen atoms—for example alkaloids like morphine and quinine—have the potential to treat a broad range of human diseases. However, the presence of a nitrogen atom in a target molecule can complicate its chemical synthesis because of the basicity of nitrogen atoms and their susceptibility to oxidation. Obtaining such compounds by chemical synthesis can be further complicated by the presence of multiple nitrogen atoms, but it can be done by the selective introduction and removal of functional groups that mitigate basicity. Here we use such a strategy to complete the chemical syntheses of citrinalinB and cyclopiamineB. The chemical connections that have been realized as a result of these syntheses, in addition to the isolation of both 17-hydroxycitrinalinB and citrinalinC (which contains a bicyclo[2.2.2]diazaoctane structural unit) through carbon-13 feeding studies, support the existence of a common bicyclo[2.2.2]diazaoctane-containing biogenetic precursor to these compounds, as has been proposed previously.

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