|2,3-diMeO-P2Pol --> P2P||Bookmark|
To a solution of 2,3-diMeO-P2Pol (4.23g, 21.58mmol) in
acetone (120mL) at 0°C was added 9.0mL of Jones'reagent (2.7M
solution) dropwise. The mixture was stirred at 0°C for 1h.
Excess oxidant was destroyed by dropwise addition of IPA (3mL).
The volatiles were evaporated, and the crude ketone was isolated
via standard ethereal workup. Chromatography (elution with H:E,
4:1) gave 2.45g (60%) of 2,3-diMeO-P2P as a light oil which was
homogeneous by TLC analysis [H:E, 3:1, Rf(propanone)=0.30]
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