N-Alkynyl Pyrrole Based Total Synthesis of Shensongine A

Brandon J. Reinus; Sean M. Kerwin

doi:10.1055/s-0037-1611904

Synthesis, Table of Contents

Synthesis 2019; 51(21): 4085-4105
DOI: 10.1055/s-0037-1611904

paper

N-Alkynyl Pyrrole Based Total Synthesis of Shensongine A

Brandon J. Reinus

^aDepartment of Chemistry, University of Texas at Austin, Austin, TX 78712, USA

,

Sean M. Kerwin∗

^bDepartment of Chemistry & Biochemistry, Texas State University, San Marcos, TX 78666, USA Email: smk89@txstate.edu

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Abstract

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Abstract

A copper-catalyzed N-alkynylation of pyrrole and a gold-catalyzed spiroketalization were key steps in the total synthesis of the pyrrole spiroketal alkaloid shensongine A. The preparation of this alkaloid is concise and amenable to the rapid synthesis of a diverse library of compounds.

Key words

cross-coupling - alkynes - nitrogen heterocycles - spiroketalization - shensongine A - pyrrole spiroketal alkaloids - total synthesis

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References

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