A Copper-Catalyzed N-Alkynylation Route to 2-Substituted N-Alkynyl Pyrroles and Their Cyclization into Pyrrolo[2,1-c]oxazin-1-ones: A Formal Total Synthesis of Peramine

被引：9

作者：

Reinus, Brandon J. ^{[1
]}

Kerwin, Sean M. ^{[2
]}

机构：

[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA

[2] Texas State Univ, Dept Chem & Biochem, San Marcos, TX 78666 USA

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 11期

关键词：

cross-coupling; alkynes; nitrogen heterocycles; cyclization; peramine; COUPLING REACTIONS; ETHYL CYCLOPROPYLIDENEACETATE; ORGANIC-SYNTHESIS; ROOM-TEMPERATURE; TERMINAL ALKYNES; YNAMIDES; AMIDATION; BROMIDES; CYCLOADDITION; ARYL;

D O I：

10.1055/s-0036-1588736

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Screening of a variety of ligands and reaction conditions for the copper-catalyzed cross-coupling of alkynyl bromides with pyrroles, reveals that the use of the phenanthroline ligand 4,7-dimethoxy-1,10-phenanthroline affords a range of ynpyrroles in good to moderate yields. Furthermore, the utility of these ynpyrroles is demonstrated in the preparation of a series of pyrrolo[2,1-c][1,4]oxazin-1-ones and a formal total synthesis of the pyrrole natural product peramine.

引用

页码：2544 / 2554

页数：11

共 23 条

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