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Efficient synthesis of karrikinolide via Cu(II)-catalyzed lactonization

Author:
Matsuo, Kazumasa, Shindo, Mitsuru
Source:
Tetrahedron 2011 v.67 no.5 pp. 971-975
ISSN:
0040-4020
Subject:
bromination, burning, chemical structure, copper, olefin, plant growth substances, smoke
Abstract:
The efficient total synthesis of karrikinolide (KAR₁), 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 KAR₁ in acceptable yield.
Agid:
1093418