3base (Hive Bee)
06-10-02 12:27
No 319365
      2,3-diMeO-P2Pol --> P2P  Bookmark   

To a solution of 2,3-diMeO-P2Pol (4.23g, 21.58mmol) in
acetone (120mL) at 0C was added 9.0mL of Jones'reagent (2.7M
solution) dropwise. The mixture was stirred at 0C 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