Synthesis of Ampelopsin F

Structure of Ampelopsin F

C28H22O6

Principal investigatorScott A. Snyder
Publication year2007
Synthesis typeTotal
Number of steps 12 (linear)
References
Part 1 of 1
intermediate structure
NaBH4
MeOH
0 °C, 30 min
intermediate structure
PBr3, Pyr
Et2O
40 °C, 3 h, 93% (2 steps)
intermediate structure
NBS
CH2Cl2
0 °C, 60 min, 95%
intermediate structure
HP(O)(OEt)2, TMS2NK
THF
0 °C to RT, 12.5 h, 91%
intermediate structure + intermediate structure
KOt-Bu
THF
-78 °C to RT, 13.5 h, 98%
intermediate structure + intermediate structure
n-BuLi
THF
-78 °C to RT, 5.5 h, 71%
intermediate structure + intermediate structure
TsOH
CH2Cl2
-50 °C to RT, 17.5 h, 65%
See the Prins Reaction
intermediate structure
mCPBA, NaHCO3
CH2Cl2
0 °C to RT, 3 h, 78%
intermediate structure
KOH
t-BuOH, CCl4, H2O
80 °C, 12 h, 52%
intermediate structure
Br2
CH2Cl2
-78 °C to RT, 4 h, 53%
intermediate structure
TMS3SiH, AIBN
PhMe
100 °C, 8 h, 89%
intermediate structure
BBr3
CH2Cl2
0 °C to RT, 19 h, 90%
intermediate structure