TY - JOUR
T1 - Efficient synthesis of karrikinolide via Cu(II)-catalyzed lactonization
AU - Matsuo, Kazumasa
AU - Shindo, Mitsuru
N1 - Funding Information:
This research was partially supported by a Grant-in-Aid for Scientific Research (B) (22390002) and the Program for Promotion of Basic and Applied Research for Innovations in the Bio-oriented Industry (BRAIN). K.M. additionally acknowledges the support of the JSPS.
PY - 2011/2/4
Y1 - 2011/2/4
N2 - 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.
AB - 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.
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U2 - 10.1016/j.tet.2010.11.108
DO - 10.1016/j.tet.2010.11.108
M3 - Article
AN - SCOPUS:78651364751
SN - 0040-4020
VL - 67
SP - 971
EP - 975
JO - Tetrahedron
JF - Tetrahedron
IS - 5
ER -