Highly Regio- and Diastereoselective Phosphine-Catalyzed [2+4] Annulation of Benzofuran-Derived Azadienes with Allyl Carbonates: Access to Spiro[benzofuran-cyclohexanes]

被引:4
|
作者
Huang, Yifei [1 ]
Tan, Mengting [1 ]
Wang, Nengzhong [1 ]
Zhang, Yufei [1 ]
Yao, Hui [1 ]
Xiao, Xiao [2 ]
Huang, Nianyu [1 ]
Zou, Kun [1 ]
机构
[1] China Three Gorges Univ, Coll Biol & Pharmaceut Sci, Hubei Key Lab Nat Prod Res & Dev, Key Lab Funct Yeast China Natl Light Ind, Yichang 443002, Peoples R China
[2] Zhejiang Univ Technol, Inst Pharmaceut Sci & Technol, Hangzhou 310014, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 18期
基金
中国国家自然科学基金; 湖北省教育厅重点项目;
关键词
CONSTRUCTION; GRISEOFULVIN; HETEROCYCLES; FILIFOLINOL; DERIVATIVES;
D O I
10.1021/acs.joc.3c01154
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel highly regio-and diastereoselective phosphine-catalyzed [2 + 4] annulation of benzofuran-derived azadienes (BDAs) with acidic hydrogen-tethered allyl carbonates has been developed ingeniously. A range of functionalized spiro[benzofuran-cyclohexane] derivatives with two consecutive stereocenters were smoothly obtained in moderate to excellent yields under mild reaction conditions from readily available materials. Moreover, this method is a practical and scalable strategy that creates the core structural motif of the fungistatic drug, griseofulvin.
引用
收藏
页码:13030 / 13041
页数:12
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