Enantioselective syn and anti Homocrotylation of Aldehydes: Application to the Formal Synthesis of Spongidepsin

被引：29
|
作者：
Lin, Hongkun [1 ]
Tian, Leiming [1 ]
Krauss, Isaac J. [1 ]
机构：
[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 40期
基金：
美国国家科学基金会;
关键词：
DIASTEREOSELECTIVE SYNTHESIS; CYCLOPROPYLBORONIC ACIDS; ASYMMETRIC CYCLOPROPANATION; STEREOSELECTIVE-SYNTHESIS; (-)-SPONGIDEPSIN; ALCOHOLS; COMPLEXES; ESTERS; HOMOCROTYLBORATION; HOMOALLYLBORATION;
D O I：
10.1021/jacs.5b08858
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Whereas crotylboration has been a useful method for synthesis of stereochemically complex products, we have shown that homocrotylboration can be achieved with cyclopropanated crotylation reagents, and that the stereo-selectivity of the reaction can be predicted by analogous models. This paper presents a full account of this work, including the first examples of asymmetric anti homocrotylation. The scope of this reaction is demonstrated with highly enantioselective homocrotylation of both aliphatic and aromatic aldehydes, as well as double diastereoselection studies. An application of the synthesis of the marine natural product spongidepsin is presented, as well as streamlined syntheses of homocrotylation reagents.
引用
收藏
页码：13176 / 13182
页数：7
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