对映体纯的顺式和反式紫檀素骨架的手性光学性质及合成

Chiroptical properties and synthesis of enantiopure cis and trans pterocarpan skeleton.

作者信息

Kiss Loránd, Kurtán Tibor, Antus Sándor, Bényei Attila

机构信息

Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary.

出版信息

Chirality. 2003 Jun;15(6):558-63. doi: 10.1002/chir.10235.

DOI:10.1002/chir.10235

PMID:12774295

Abstract

The first enantioselective synthesis of trans-(6aS,11aR)-pterocarpan [(+)-2] and its conversion to cis-(6aS,11aS)-pterocarpan [(+)-1] was achieved starting from racemic 2'-benzyloxyflavanone (rac-3). Their stereochemistry was deduced by X-ray analysis of the ketal intermediate (-)-5a. The CD study of (+)-1 and (+)-2 allows the configurational assignment of similar pterocarpan derivatives by CD spectroscopy.

摘要

从外消旋2'-苄氧基黄烷酮（rac-3）出发，首次实现了反式-(6aS,11aR)-紫檀烷[(+)-2]的对映选择性合成及其向顺式-(6aS,11aS)-紫檀烷[(+)-1]的转化。通过缩酮中间体(-)-5a的X射线分析推导了它们的立体化学。对(+)-1和(+)-2的圆二色性研究使得能够通过圆二色光谱对类似的紫檀烷衍生物进行构型归属。