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Abstract
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.
Original language | English |
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Pages (from-to) | 4823-4826 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 51 |
Issue number | 37 |
DOIs | |
Publication status | Published - 1 Sept 2010 |
Keywords
- Total synthesis
- Free radical cyclisation
- Dearomatisation
- Electron-rich aromatics
- Acylphloroglucinol
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Dive into the research topics of 'Expedient synthesis of ialibinones A and B by manganese(III)-mediated oxidative free radical cyclisation'. Together they form a unique fingerprint.Projects
- 1 Finished
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Rapid synthesis of complex bioactive alkaloids
Simpkins, N.
Engineering & Physical Science Research Council
1/10/09 → 30/09/12
Project: Research Councils