Synthesis of Cyclophellitol

Structure of Cyclophellitol

C7H12O5

Principal investigatorKen-Ichi Sato
Publication year1994
Synthesis typeTotal
Number of steps 13 (linear)
References
Part 1 of 1
intermediate structure
i-Pr2NLi
THF, CH2Cl2
-78 °C, , 82%
intermediate structure
NaBH4
DMSO
80 °C, , 82%
intermediate structure
Ac2O
Pyr
RT, , 100%
intermediate structure
NBS, BaCO3
CCl4
Reflux
intermediate structure
NaI
Acetone
Reflux
intermediate structure
DBU
DMSO
80 °C, 60 min, 56% (3 steps)
intermediate structure
HgCl2
Acetone, H2O
Reflux, 60 min
intermediate structure
MsCl, Et3N
CH2Cl2
0 °C, , 86% (2 steps)
intermediate structure
NaBH4, CeCl3.7H2O
EtOH, CH2Cl2
-78 °C, , 67%
See the Luche Reduction
intermediate structure
TBSCl, Imidazole
DMF
40 °C, , 94%
intermediate structure
KOH
EtOH
RT, 20 min, 80%
intermediate structure
mCPBA
DCE
40 °C, 24 h, 84%
intermediate structure
AcOH
H2O
RT, 60 min, 100%
intermediate structure