Synthesis 2017; 49(11): 2544-2554
DOI: 10.1055/s-0036-1588736
paper
© Georg Thieme Verlag Stuttgart · New York

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

Brandon J. Reinus
a   Department of Chemistry, University of Texas at Austin, Austin, TX 78712, USA
,
Sean M. Kerwin*
b   Department of Chemistry & Biochemistry, Texas State University, San Marcos, TX 78666, USA   Email: smk89@txstate.edu
› Author Affiliations
Further Information

Publication History

Received: 01 January 2017

Accepted after revision: 10 February 2017

Publication Date:
14 March 2017 (online)


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

 
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