Carbocyclic thromboxane A2
Carbocyclic thromboxane A2
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碳环血栓素A2
DOI：
10.1021/ja00524a028
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发表时间：
1980
影响因子：
15
通讯作者：
D. Claremon
中科院分区：
文献类型：
--
作者：
K. Nicolaou;R. Magolda;D. Claremon
碳环血栓烷A2（CTA 2）（5）和羟基差向异构体（5 b）的全合成已实现外消旋和光学活性形式。双环[3.1. 1]2-庚酮（6）通过两种不同的路线合成得到关键中间体7，该中间体7通过铜酸盐1，4加成引入低侧链，然后通过醛官能团的同系化和Wittig反应完成顶链，有效地转化为碳环血栓烷A2骨架。得到的稳定的血栓烷A2类似物5和5 b表现出有趣的和有效的生物学特性。
The total synthesis of carbocyclic thromboxane A2 (CTA2)(5) and itshydroxy epimer (5b) has been achieved both in racemic and optically active forms. Bicyclo [3.1. 1] heptan-2-one (6), synthesized by two alternative routes, was converted to the key intermediate 7, which was efficiently transformed to thecarbocyclic thromboxane A2 skeleton by a cuprate 1, 4 addition to introduce the lower side chain followed byhomologation of the aldehyde function and Wittig reaction to complete the top chain. The resulting stable thromboxane A2 analogues 5 and 5b exhibited interesting and potent biological properties.