|1pot: veratrole --> 2,3-diMeO-P2Pol||Bookmark|
To a solution of veratrole (6.90g, 50.00mmol) in 25 mL of THF at
0°C was added 20mL of n-butyllithium (2.5M solution in hexanes).
The resulting mixture was stirred at 0°C for 3h. Propene oxide
(2.90g, 50.00mmol) was added dropwise to the reaction mixture.
The resulting mixture was allowed to warm to rt and stirred at rt
for 8h. Standard ethereal workup, followed by chromatography
(elution with H:E, 1:1), gave 2.27g of recovered veratrole (33%)
and 5.03g (51%) of 2,3-diMeO-P2Pol as a light oil which was
homogeneous by TLC analysis [H:E, 2:3, Rf(propanol)=0.38]
j org chem, 1997 62(20): 6928-6951
"Use of Conjugated Dienones in Cyclialkylations:
Total Syntheses of Arucadiol, 1,2-Didehydromiltirone,
(±)-Hinokione, (±)-Nimbidiol, Sageone, and Miltirone"
George Majetich, Shuang Liu, Jing Fang,
David Siesel, Yong Zhang