Barton esters for initiator-free radical cyclisation with heteroaromatic substitution

Research output: Contribution to journalArticlepeer-review

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.
Original languageEnglish
Article number1682
Pages (from-to)1672
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume11
Early online date23 Jan 2013
DOIs
Publication statusPublished - 9 Nov 2013
Externally publishedYes

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