Synthesis of 6a-hydroxypterocarpans via intramolecular benzoin condensation

被引：4

作者：

Malik, Neha ^{[1
]}

Erhardt, Paul ^{[1
]}

机构：

[1] Univ Toledo, Coll Pharm & Pharmaceut Sci, Dept Med & Biol Chem, Ctr Drug Design & Dev, Toledo, OH 43606 USA

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 31期

基金：

美国农业部;

关键词：

Glyceollins; Glycinol; 6a-Hydroxypterocarpans; Intramolecular benzoin cyclization; TRIAZOLIUM SALTS; GLYCEOLLIN I; PHYTOALEXINS; ISOFLAVONOIDS; PTEROCARPANS;

D O I：

10.1016/j.tetlet.2013.05.121

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel approach for the syntheses of 6a-hydroxypterocarpans is reported. Its practicality is demonstrated by the synthesis of (+/-)-glycinol. The main feature is an intramolecular benzoin condensation catalyzed by nucleophilic carbenes to initiate assembly of the benzopyran and establish the 6a-hydroxy center. In addition, a one-pot method was developed to form an epoxide that facilitates subsequent cyclization leading to the benzofuran and direct production of (+/-)-glycinol. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：4121 / 4124

页数：4

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