Issue 7, 2021
From the journal:

Chemical Communications

Regioselective side-chain amination of 2-alkyl azacycles by radical translocation: total synthesis of tetraponerine T8†

Samuel D. Griggs, ORCID logo a   Alejandro Martin-Roncero, ORCID logo a   Adam Nelson ORCID logo *a  and  Stephen P. Marsden ORCID logo *a  

* Corresponding authors

a Department of Chemistry, University of Leeds, Leeds, UK
E-mail: s.p.marsden@leeds.ac.uk

Abstract

The regioselective γ-C–H amination of the side-chain of saturated 2-alkyl nitrogen heterocycles is reported, proceeding through a sulfamide-directed 1,6-radical translocation. The practicality of this rapid access to 1,3-diamines is highlighted in a short synthesis of the alkaloid tetraponerine T8 and non-natural analogues.

Graphical abstract: Regioselective side-chain amination of 2-alkyl azacycles by radical translocation: total synthesis of tetraponerine T8

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Article information

DOI
https://doi.org/10.1039/D0CC07625B
Article type
Communication
Submitted
20 Nov 2020
Accepted
18 Dec 2020
First published
18 Dec 2020

Chem. Commun., 2021,57, 919-922

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Regioselective side-chain amination of 2-alkyl azacycles by radical translocation: total synthesis of tetraponerine T8

S. D. Griggs, A. Martin-Roncero, A. Nelson and S. P. Marsden, Chem. Commun., 2021, 57, 919 DOI: 10.1039/D0CC07625B

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