Synthesis of substituted phenanthrofurans

被引：16

作者：

Chan, Chieh-Kai ^{[1
]}

Chen, Yi-Chia ^{[1
]}

Chen, Yeh-Long ^{[1
]}

Chang, Meng-Yang ^{[1
]}

机构：

[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan

来源：

TETRAHEDRON | 2015年 / 71卷 / 49期

关键词：

Phenanthrofurans; Cycloisomerization; Scholl annulation; CATALYZED CYCLOISOMERIZATION; 1,3-DICARBONYL COMPOUNDS; TETRASUBSTITUTED FURANS; DOMINO REACTION; ARYL IODIDES; DERIVATIVES; ARYLATION; ALLYLATION; BONDS;

D O I：

10.1016/j.tet.2015.10.060

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A three-step protocol toward phenanthrofurans 1 starting with deoxybenzoins 3 is developed with moderate to good yield. A facile process is carried out for the (1) alpha-propargylation of 3 with NaH and propargyl bromide 2 in refluxing THF, (2) Bi(OTf)(3)-mediated cycloisomerization of gamma-ynones 4 with 4 angstrom molecular sieves in MeNO2 at it, and (3) photolytic Scholl annulation of 2,3-diarylfurans 5 with I-2 in EtOAc at rt. The key structures of 1 are confirmed by X-ray crystallographic analysis. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：9187 / 9195

页数：9

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