Total Synthesis of (+)-Aplykurodinone-1.
Total Synthesis of (+)-Aplykurodinone-1.
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( )-Aplykurodinone 的全合成 1
DOI：
10.1021/acs.orglett.7b02350
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发表时间：
2017
期刊：
影响因子：
--
通讯作者：
Fayang G. Qiu
中科院分区：
文献类型：
--
作者：
Bo Xu;Wen Xun;Tingzhong Wang;Fayang G. Qiu
以（R）-香茅酸和（R）-藜芦烯醇为起始原料，经11步反应合成了高度降解的海洋甾体化合物（+）-紫堇酮-1，总收率为19%，具有良好的立体化学控制。除了诸如Ireland-Claisen重排、分子内羰基-烯环化和分子内Michael加成的特征之外，本发明的合成策略在不使用保护基团的情况下完成。
Starting from (R)-citronellic acid and (R)-seudenol, the total synthesis of (+)-aplykurodinone-1, a highly degraded marine steroid, has been achieved in 11 steps and in 19% overall yield with excellent stereochemical control. In addition to the features such as an Ireland-Claisen rearrangement, an intramolecular carbonyl-ene cyclization, and an intramolecular Michael addition, the present synthetic strategy is accomplished without the use of protecting groups.