Chalcones are easily accessible synthetic building blocks that are used in various heterocyclic syntheses. The rearrangement reaction using an oxidant is a characteristic conversion of chalcones, but applications to organic synthesis have been limited. Here, the development of a new method for synthesizing 3-acylindoles and azaisoflavones using a chalcone rearrangement strategy with hypervalent iodine reagents was described. Furthermore, the obtained new insight was applied to the selective synthesis of two benzofuran isomers from 2-hydroxychalcone derivatives and have demonstrated this method to the synthesis of the natural product, puerariafuran.

20 Oct 2017·The Journal of Organic ChemistryQ2 · CHEMISTRY

Collective Syntheses of 2-(3-Methylbenzofuran-2-yl)phenol-Derived Natural Products by a Cascade [3,3]-Sigmatropic Rearrangement/Aromatization Strategy

Q2 · CHEMISTRY

Article

Author: Jiang, Chongguo ; Li, Wei ; Zhang, Xinhang ; Du, Chuan ; Liu, Yongxiang ; Liu, Chengjun ; Wang, Yanshi ; Tang, Yingzhan ; Lin, Jingsheng ; Peng, Xiaoshi ; Cheng, Maosheng

A cascade [3,3]-sigmatropic rearrangement/aromatization strategy to the synthesis of 2-(3-methylbenzofuran-2-yl)phenol derivatives was developed and applied to the collective syntheses of seven 2-arylbenzofuran-containing natural products, namely glycybenzofuran, glycyuralin E, lespedezol A₁, puerariafuran, 7,2',4'-trihydroxy-3-benzofurancarboxylic acid, coumestrol, and 4'-O-methylcoumestrol. Among them, the total syntheses of glycybenzofuran, glycyuralin E, puerariafuran, 7,2',4'-trihydroxy-3-benzofurancarboxylic acid, and 4'-O-methylcoumestrol were reported for the first time. The practicality of this novel strategy in preparation of the key intermediates was demonstrated by performing the reaction on gram scale and by synthesizing a series of natural products with 2-(3-methylbenzofuran-2-yl)phenol scaffolds in a common strategy.

01 Apr 2012·Journal of Natural MedicinesQ4 · MEDICINE

Solalyratins A and B, new anti-inflammatory metabolites from Solanum lyratum

Q4 · MEDICINE

Article

Author: Yan Yang ; Fang Yao ; Qun-Ying Yu ; Sheng-Jun Dai ; De-Wu Zhang

A new coumestan (solalyratin A, 1) and a novel cyclic eight-membered α,β-unsaturated ketone (solalyratin B, 3), together with three known compounds, puerariafuran (2), coumestrol (4) and 9-hydroxy-2',2'-dimethylpyrano[5',6':2,3]-coumestan (5), were isolated from the whole plant of Solanum lyratum. Their structures were elucidated on the basis of spectroscopic analyses. In vitro, compounds 1-5 showed anti-inflammatory activities, with IC(50) values in the range 6.3-9.1 μM.

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