Total synthesis of linoxepin facilitated by a Ni-catalyzed tandem reductive cyclization

被引：12

作者：

Cao, Jing-Si ^{[1
]}

Zeng, Jing ^{[1
]}

Xiao, Jian ^{[1
]}

Wang, Xiao-Han ^{[2
]}

Wang, Ya-Wen ^{[1
]}

Peng, Yu ^{[1
]}

机构：

[1] Southwest Jiaotong Univ, Sichuan Engn Res Ctr Biomimet Synth Nat Drugs, Sch Life Sci & Engn, Chengdu 610031, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2022年 / 58卷 / 52期

基金：

中国国家自然科学基金;

关键词：

UNACTIVATED ALKYL BROMIDES; COUPLING REACTIONS; ROOM-TEMPERATURE; ARYL IODIDES; LIGNAN; MECHANISMS; ALKENES; BIOLOGY; HALIDES; CORE;

D O I：

10.1039/d2cc02221d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A nickel-catalyzed reductive cyclization was developed to construct the tricyclic core embedded in linoxepin, a cyclolignan with a unique benzoxepin ring. The generated diastereodivergent acetals could be converted to the common unsaturated lactone, thus allowing a racemic synthesis of this molecule after incorporation of the remaining aromatic ring. This strategy with a late-stage installation of the D-ring led to the facile production of several linoxepin analogs as well.

引用

页码：7273 / 7276

页数：4

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[1] Mechanisms of Nickel-Catalyzed Coupling Reactions and Applications in Alkene Functionalization [J].