Synthesis of Glycyrol

Structure of Glycyrol

C21H18O6

Principal investigatorHak Sung Kim
Publication year2008
Synthesis typeTotal
Number of steps 12 (3 parts)
References
Part 1 of 3
intermediate structure
i-Pr2NEt, MeOCH2Cl
CH2Cl2
0 °C, 60 min
intermediate structure
K2CO3, Me2SO4
Acetone
80 °C, 60 min, 90% (2 steps)
intermediate structure
I2
MeOH
RT, 2 h, 66%
intermediate structure + intermediate structure
K2CO3
Acetone
Reflux, 8 h, 66%
intermediate structure
PhNEt2
Reflux, 60 min, 64%
intermediate structure
NaH, EtOCO2Et
0 °C to Reflux, 5 h, 68%
intermediate structure
Part 2 of 3
intermediate structure
BnBr, K2CO3
Acetone
RT, 6 h, 95%
intermediate structure
NaBO3.4H2O
AcOH
40-45 °C, 8.5 h, 100%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
Na2CO3
H2O
RT, 2.5 h
intermediate structure
DMF
Reflux, 60 min, 87% (2 steps)
intermediate structure
Et3N, Pd(OAc)2
PhMe
Reflux, 6 h, 87%
See the Heck Coupling
intermediate structure
AlCl3
CH2Cl2, PhNMe2
0 to 50 °C, 30 min, 68%
intermediate structure