Synthesis of Quadrone

Structure of Quadrone

C15H20O3

Principal investigatorSteven D. Burke
Publication year1982
Synthesis typeFormal
Number of steps 21 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
THF
-78 °C to RT, 4.5 h, 77%
intermediate structure
LiAlH4
Et2O
0 °C, 4 h, 99%
intermediate structure
VinylOEt, Hg(OAc)2
Reflux, ON
intermediate structure
187 to 200 °C, 6 h, 94% (2 steps)
intermediate structure
CrO3, H2SO4
Acetone, H2O
0 °C to RT, 8.5 h, 98%
See the Jones Oxidation
intermediate structure
(COCl)2
PhH
RT, 8.5 h
intermediate structure
TiCl4
CH2Cl2
-30 °C to RT, 16 h, 84% (2 steps)
intermediate structure
OsO4, NMO
Acetone, H2O
intermediate structure
NaIO4
THF, H2O
94% (2 steps)
intermediate structure
Morpholine, TsOH
PhH
Reflux, , 92%
intermediate structure
NaOH, Dibenzo-18-crown-6
PhH
Reflux, , 96%
intermediate structure
TsOH, (CH2OH)2
PhH
Reflux
intermediate structure
t-BuOOH, NaOH
MeOH, H2O
RT, , 89% (2 steps)
intermediate structure
NH2NH2
AcOH, MeOH
92%
intermediate structure
VinylOEt, Hg(OAc)2
Xylene(s)
250 °C, , 90%
intermediate structure
H2, Pd/C
EtOH
RT, , 100%
intermediate structure
KOAc
Ac2O
Reflux
intermediate structure
OsO4, NaIO4
THF, H2O
57% (2 steps)
intermediate structure
CrO3, H2SO4
H2O
See the Jones Oxidation
intermediate structure
CH2N2
Et2O
60% (2 steps)
intermediate structure
Remaining...
24% (6 steps)
"See : J. Am. Chem. Soc. 1981, 103, 4136."
intermediate structure