Synthesis of Paeoniflorigenin

Structure of Paeoniflorigenin

C17H18O6

Principal investigatorElias J. Corey
Publication year1993
Synthesis typeTotal
Number of steps 13 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
Mn3O(OAc)7, KOAc
MeCN
RT, 90 min, 48%
intermediate structure
TfCl, Et3N
CH2Cl2
0 °C, 10 min, 70%
intermediate structure
mCPBA, NaHCO3
CH2Cl2
RT, 15 h, 81%
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C, 30 min, 78%
intermediate structure
TMSOTf
CH2Cl2
-78 °C, 60 min, 35%
intermediate structure
HCrO3Cl.Pyr
CH2Cl2
RT, 30 min, 100%
intermediate structure
SmI2
THF
-45 °C, 10 h, 90%
intermediate structure
TMSCN
CH2Cl2
RT, 15 h, 82%
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C, 30 min, 86%
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C, 60 min, 81%
intermediate structure
BzCl, Pyr
CH2Cl2
RT, 3 h, 96%
intermediate structure
HCl
THF
0 °C, 6 h, 100%
intermediate structure
HF
MeCN
RT, 2 h, 91%
intermediate structure