Journal
TETRAHEDRON
Volume 67, Issue 5, Pages 971-975Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.11.108
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Funding
- Program for Promotion of Basic and Applied Research for Innovations in the Bio-oriented Industry (BRAIN)
- JSPS
- [22390002]
- Grants-in-Aid for Scientific Research [22390002] Funding Source: KAKEN
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The efficient total synthesis of karrikinolide (KAR(1)), a potent plant growth regulator discovered in smoke from burning plant material, is described. 3-Hydroxy-4-pyranone, prepared from D-xylose, was subjected to a Cu(II)-catalyzed transesterification-Wittig lactonization to afford the dihydrofuropyran in good yield. Finally, radical bromination, followed by olefin formation, provided KAR(1) in acceptable yield. (C) 2010 Elsevier Ltd. All rights reserved.
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