Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment
Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment
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DOI：
10.3762/bjoc.16.64
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发表时间：
2020-04-14
影响因子：
2.7
通讯作者：
Kalesse, Markus
中科院分区：
文献类型：
--
作者：
Geldsetzer, Jan;Kalesse, Markus
本文报道了软骨素（1）的（Z）-烯酰胺片段的立体选择性合成。酰胺3和（Z）-溴化物4之间的Buchwald型偶联用于产生所需片段。以D-核糖酸-1，4-内酯为起始原料，经七步反应合成了含有三个手性中心的酰胺3。（Z）-溴乙烯4可以从4-羟基苯甲醛分四步得到。在用碘化亚铜（I）、K2 CO 3和N，N '-二甲基乙烷-1，2-二胺进行大量实验后，实现了两个片段之间的关键交叉偶联。
The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was obtained through a seven-step sequence starting from D-ribonic acid-1,4-lactone. The (Z)-vinyl bromide 4 is accessible in four steps from 4-hydroxybenzaldehyde. The pivotal cross coupling between both fragments was achieved after extensive experimentation with copper(I) iodide, K2CO3 and N,N'-dimethylethane-1,2-diamine.