Synthesis of Natural Products Containing Cyclohexane Units Utilizing the Ferrier Carbocyclization Reaction
Synthesis of Natural Products Containing Cyclohexane Units Utilizing the Ferrier Carbocyclization Reaction
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DOI：
10.1002/tcr.201402024
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发表时间：
2014-08-01
期刊：
影响因子：
6.6
通讯作者：
Sato，Takaaki
中科院分区：
文献类型：
--
作者：
Chida，Noritaka;Sato，Takaaki
Ferrier 碳环化反应是碳水化合物最强大的转化之一。该反应从己醛糖提供对映体纯的环己酮衍生物，并且在从碳水化合物手性池合成含环己烷的天然产物中特别有用。我们研究了利用 Ferrier 碳环化反应合成天然产物。本介绍简要概述了费里尔碳环化及其在天然产物合成中的应用。 Ferrier 碳环化反应的实用性和多功能性通过从碳水化合物开始合成潮霉素 A、石蒜素、放线菌素、加兰他敏和吗啡来展示。
The Ferrier carbocyclization reaction is one of the most powerful transformations of carbohydrates. This reaction provides enantiomerically pure cyclohexanone derivatives from aldohexoses, and is particularly useful in the chiral pool synthesis of cyclohexane‐containing natural products from carbohydrates. We have investigated the synthesis of natural products utilizing the Ferrier carbocyclization reaction. This account provides a brief overview of the Ferrier carbocyclization and its application to natural product synthesis. The utility and versatility of the Ferrier carbocyclization reaction are showcased with the syntheses of hygromycin A, lycoricidine, actinobolin, galanthamine, and morphine starting from carbohydrates.