Total synthesis of marine natural products without using protecting groups
Total synthesis of marine natural products without using protecting groups
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DOI：
10.1038/nature05569
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发表时间：
2007-03-22
期刊：
影响因子：
64.8
通讯作者：
Richter, Jeremy M.
中科院分区：
文献类型：
--
作者：
Baran, Phil S.;Maimone, Thomas J.;Richter, Jeremy M.
在过去的50年里，有机合成领域取得了惊人的进步，但化学家们仍然在努力设计合成路线，使他们能够获得足够数量的复杂分子用于生物和医学研究。因此，全合成越来越多地集中在以最有效的方式制备天然产物。在这里，我们描述了hapalindole，fischerindole，welwitindolinone和ambigine家族的成员，每个构建不需要保护基团-使用这样的基团大大增加了成本和合成的复杂性的反式规模，对映选择性，全合成。因此，以前需要20个或更多步骤来合成毫克量外消旋的分子现在可以在10个步骤或更少的步骤中以显著量的单一对映体获得。通过本文所展示的一般原理的扩展，应该可以在不使用保护基团的情况下获得其他复杂的分子结构。
The field of organic synthesis has made phenomenal advances in the past fifty years, yet chemists still struggle to design synthetic routes that will enable them to obtain sufficient quantities of complex molecules for biological and medical studies. Total synthesis is therefore increasingly focused on preparing natural products in the most efficient manner possible. Here we describe the preparative-scale, enantioselective, total syntheses of members of the hapalindole, fischerindole, welwitindolinone and ambiguine families, each constructed without the need for protecting groups - the use of such groups adds considerably to the cost and complexity of syntheses. As a consequence, molecules that have previously required twenty or more steps to synthesize racemically in milligram amounts can now be obtained as single enantiomers in significant quantities in ten steps or less. Through the extension of the general principles demonstrated here, it should be possible to access other complex molecular architectures without using protecting groups.