(-)-idesolide 的全合成与绝对构型确定。

Total synthesis and determination of the absolute configuration of (-)-idesolide.

机构信息

Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan.

出版信息

Org Lett. 2010 Mar 5;12(5):980-3. doi: 10.1021/ol9029676.

DOI:10.1021/ol9029676

PMID:20136117

Abstract

The first total synthesis of (-)-idesolide was achieved via organocatalytic, enantioselective oxidative kinetic resolution (OKR) using (1S,4S)-4-Bn-1-Bu-AZADOH- and AZADO-catalyzed dimerization of (S)-(-)-methyl 1-hydroxy-6-oxo-2-cyclohexenecarboxylate. The absolute configuration of (-)-idesolide is determined to be 2R,2'S,3aS,7aR.

摘要

首次实现了（-）-idesolide 的全合成，方法是通过（1S,4S）-4-Bn-1-Bu-AZADOH 和 AZADO 催化的（S）-（-）-甲基 1-羟基-6-氧代-2-环己烯羧酸酯的二聚反应，进行有机催化、对映选择性氧化动力学拆分（OKR）。（-）-idesolide 的绝对构型被确定为 2R,2'S,3aS,7aR。