Synthesis of Quadrone

Structure of Quadrone

C15H20O3

Principal investigatorEiichi Yoshii
Publication year1983
Synthesis typeFormal
Number of steps 11 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
CH2Cl2
-78 °C, 7 h, 67%
intermediate structure
  1. i-Pr2NLi
  2. TMSCl
THF
-78 °C to RT, 90 min, 98%
intermediate structure
MeOCH2Cl, CH2I2, Zn-Cu
CH2Cl2
0 °C to RT, 4.5 h, 60%
intermediate structure
Propargyl bromide, Al, HgCl2
THF, Et2O
-78 to -40 °C, 90 min, 50%
intermediate structure
HCO2H
RT, 40 h
intermediate structure
HCrO3Cl.Pyr
CH2Cl2
RT, 10 h, 31% (2 steps)
intermediate structure
HgO, H2SO4
MeOH, H2O
60 °C, 60 min, 100%
intermediate structure
NaOt-Amyl
PhH
Reflux, 3.5 h, 89%
intermediate structure
BBr3
CH2Cl2
-78 to -20 °C, 24 h
intermediate structure
CrO3, H2SO4
Acetone, H2O
RT, 30 min, 49% (2 steps)
See the Jones Oxidation
intermediate structure
Remaining...
24% (5 steps)
"See : J. Am. Chem. Soc. 1981, 103, 4136."
intermediate structure