Synthesis and Applications of Hajos-Parrish Ketone Isomers.
Synthesis and Applications of Hajos-Parrish Ketone Isomers.
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DOI：
10.1002/anie.201500925
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发表时间：
2015-06-26
期刊：
影响因子：
--
通讯作者：
Snyder SA
中科院分区：
文献类型：
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作者：
Eagan JM;Hori M;Wu J;Kanyiva KS;Snyder SA
Although numerous natural products possess ring systems and functionality for which “iso-Hajos–Parrish” ketones would be of value, such building blocks have not been exploited to the same degree as the more typical Hajos–Parrish hydrindane. Herein we outline an efficient three-step synthesis of such materials fueled by a simple method for the rapid preparation of highly functionalized cyclopentenones, several of which are new chemical entities that would be challenging to access through other approaches. We then show how one iso-Hajos–Parrish ketone can be converted into two distinct natural product analogs as well as one natural product. As one indication of the value of these new building blocks, that latter target was obtained in 10 steps, having previously been accessed in 18 steps using the Hajos–Parrish ketone.
