Fully reagent-controlled asymmetric synthesis of (-)-spongidepsin via the Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction)

被引：49
|
作者：
Zhu, Gangguo [1 ]
Negishi, Ei-ichi [1 ]
机构：
[1] Purdue Univ, Herbert C Brown Labs Chem, W Lafayette, IN 47907 USA
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 15期
关键词：
D O I：
10.1021/ol0707259
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The ZACA reaction has been shown to proceed satisfactorily with internally OH-substituted 1-alkenes, provided that the OH group is unprotected and non-allylic. This reaction was used for reagent-controlled asymmetric construction of 3. Allylic alcohol was converted to 2 in seven steps via iterative ZACA processes and simple chromatography. (-)-Spongidepsin (1) was synthesized by using 2 and 3 through application of the esterification-amidation-ring-closing metathesis protocol previously reported.
引用
收藏
页码：2771 / 2774
页数：4
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