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通过非对映选择性共轭加成到手性富马酸酯实现(-)-二氢原地衣甾酸的全合成。

Total synthesis of (-)-dihydroprotolichesterenic acid via diastereoselective conjugate addition to chiral fumarates.

作者信息

Hethcox J Caleb, Shanahan Charles S, Martin Stephen F

机构信息

Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712.

出版信息

Tetrahedron Lett. 2013 Apr 17;54(16):2074-2076. doi: 10.1016/j.tetlet.2013.02.014. Epub 2013 Feb 11.

DOI:10.1016/j.tetlet.2013.02.014
PMID:23539490
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3607549/
Abstract

A diastereoselective conjugate addition of a variety of monoorganocuprates, Li[RCuI], to chiral fumarates to provide funtionalized succinates has been developed. The utility of this reaction is demonstrated in a concise total synthesis of (-)-dihydroprotolichesterenic acid that required only four steps and proceeded in an overall 31% yield.

摘要

已开发出一种将多种单有机铜酸盐Li[RCuI]与手性富马酸酯进行非对映选择性共轭加成反应,以提供功能化琥珀酸酯的方法。该反应的实用性在(-)-二氢原地衣甾酸的简洁全合成中得到了证明,该全合成仅需四步,总收率为31%。

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