A Synthetic Approach to Rocaglamide via Reductive Cyclization of δ-Keto Nitriles.
A Synthetic Approach to Rocaglamide via Reductive Cyclization of δ-Keto Nitriles.
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DOI：
10.1002/chin.198928148
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发表时间：
1989-07
期刊：
影响因子：
--
通讯作者：
G. Kraus;James Sy
中科院分区：
文献类型：
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作者：
G. Kraus;James Sy
抗癌剂洛格列胺含有一种新型的双环[3.3.0]辛醇结构。合成该分子的方法包括通过钐介导的环化反应制备羟基酮中间体。然后，这种酮通过新颖的化学作用被转化为极好的迈克尔受体。随后的步骤导致了洛格拉胺异构体的制备。X射线测定支持我们的观点，即铜酸盐的加成具有不寻常的凹面选择性。
The anticancer agent rocaglamide contains a novel bicyclo[3.3.0]octanol structure. The approach to this molecule involved the preparation of a hydroxy ketone intermediate via a samarium-mediated cyclization. This ketone was then converted into an excellent Michael acceptor via novel chemistry. Subsequent steps led to the preparation of an isomer of rocaglamide. An X-ray determination supported our view that cuprate addition occurred with unusual concave selectivity.