Journal
TETRAHEDRON LETTERS
Volume 51, Issue 37, Pages 4823-4826Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.07.025
Keywords
Acylphloroglucinol; Dearomatisation; Free radical cyclisation; Electron-rich aromatics; Total synthesis
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Funding
- Engineering and Physical Sciences Research Council (EPSRC)
- Advantage West Midlands (AWM)
- European Regional Development Fund (ERDF)
- Engineering and Physical Sciences Research Council [EP/H013040/1] Funding Source: researchfish
- EPSRC [EP/H013040/1] Funding Source: UKRI
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The tricyclic natural products ialibinone A and ialibinone B were prepared as a 41:59 mixture in four steps starting from phloroglucinol. The synthetic sequence involved (i) acylation of phloroglucinol under Friedel-Crafts conditions, (ii) double prenylation using phase-transfer methodology, (iii) dearomatising methylation, and (iv) oxidative free radical cyclisation using manganese(III) acetate. (C) 2010 Elsevier Ltd. All rights reserved.
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