Issue 1, 2016

Synthesis of the 1,2,4-thiadiazole alkaloids polycarpathiamines A and B

Abstract

In the presence of 1 mol% of a copper(II) catalyst and air, a readily available N1-acetyl-N3-thioacylguanidine undergoes a one-pot benzylic oxidation–oxidative heterocyclization sequence to give the 3-amino-5-acyl-1,2,4-thiadiazole core of polycarpathiamines A (2) and B (3) and thus facilitating the first synthesis of both natural products. This methodology offers a straightforward alternative to the low yielding dipolar cycloaddition used to access 3-amino-5-acyl-1,2,4-thiadiazoles.

Graphical abstract: Synthesis of the 1,2,4-thiadiazole alkaloids polycarpathiamines A and B

Supplementary files

Article information

Article type
Research Article
Submitted
11 nov 2015
Accepted
27 nov 2015
First published
30 nov 2015

Org. Chem. Front., 2016,3, 38-42

Author version available

Synthesis of the 1,2,4-thiadiazole alkaloids polycarpathiamines A and B

E. K. Davison and J. Sperry, Org. Chem. Front., 2016, 3, 38 DOI: 10.1039/C5QO00367A

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