An Efficient Approach to the Total Synthesis of Ammosamide B
An Efficient Approach to the Total Synthesis of Ammosamide B
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DOI：
10.1002/ejoc.201501560
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发表时间：
2016-02
影响因子：
2.8
通讯作者：
Sheng-Wei Yang;Chun-meng Wang;Kai-Xiang Tang;Jinxin Wang;Li‐Ping Sun
中科院分区：
文献类型：
--
作者：
Sheng-Wei Yang;Chun-meng Wang;Kai-Xiang Tang;Jinxin Wang;Li‐Ping Sun
实现了氨酰胺B的全合成。该策略基于4-氯-1-甲基吲哚啉-2，3-二酮（2）的分子间Pd催化的N-芳基化，这使得能够在三个步骤内以80%的总产率构建关键的吡咯并喹啉骨架前体6。氨酰胺B的全合成是通过从市售原料开始的12个简单的转化来实现的，并且以23%的总产率进行。此外，关键前体6是合成其他含吡咯并喹啉天然产物的重要中间体。
A new approach for the total synthesis of ammosamide B was realized. The strategy is based on an intermolecular Pd-catalyzed N-arylation of 4-chloro-1-methylindoline-2,3-dione (2), which enables construction of the key pyrroloquinoline skeleton precursor 6 within three steps in an overall yield of 80 %. The ammosamide B total synthesis is achieved in 12 simple transformations by starting from a commercially available starting material and proceeds with an overall yield of 23 %. Additionally, key precursor 6 represents an important intermediate in the synthesis of other pyrroloquinoline-containing natural products.