Issue 10, 2013

Barton esters for initiator-free radical cyclisation with heteroaromatic substitution

Abstract

S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium hexafluorophosphate (HOTT) facilitates the first examples of efficient radical cyclisation with (hetero)aromatic substitution via Barton ester intermediates. Cyclopropyl and alkyl radicals allow access to five, six and seven-membered alicyclic-ring fused heterocycles with and without an additional fused cyclopropane, including the skeleton of the anti-cancer agent, cyclopropamitosene, expanded, and diazole analogues. Radical initiators are not required for cyclisation from carboxylic acid precursors.

Graphical abstract: Barton esters for initiator-free radical cyclisation with heteroaromatic substitution

Supplementary files

Article information

Article type
Paper
Submitted
28 Nov 2012
Accepted
22 Jan 2013
First published
23 Jan 2013

Org. Biomol. Chem., 2013,11, 1672-1682

Barton esters for initiator-free radical cyclisation with heteroaromatic substitution

R. Coyle, K. Fahey and F. Aldabbagh, Org. Biomol. Chem., 2013, 11, 1672 DOI: 10.1039/C3OB27313J

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