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Synthesis 2017; 49(11): 2544-2554
DOI: 10.1055/s-0036-1588736
DOI: 10.1055/s-0036-1588736
paper
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
Weitere Informationen
Publikationsverlauf
Received: 01. Januar 2017
Accepted after revision: 10. Februar 2017
Publikationsdatum:
14. März 2017 (online)
![](https://www.thieme-connect.de/media/synthesis/201711/lookinside/thumbnails/ss-2017-m0001-op_10-1055_s-0036-1588736-1.jpg)
Abstract
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.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588736.
- Supporting Information
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