Synthesis of Prostaglandin F2α

Structure of Prostaglandin F2α

C20H34O5

Principal investigatorElias J. Corey
Publication year1969
Synthesis typeTotal
Number of steps 17 (linear)
References
Part 1 of 1
intermediate structure
MeOCH2Cl, NaH
THF
-55 °C
intermediate structure
2-Chloroacrylonitrile, Cu(BF4)2
0 °C
intermediate structure
KOH
DMSO
30 °C, 14 h, 80% (3 steps)
intermediate structure
mCPBA
CH2Cl2
95%
intermediate structure
NaOH
H2O
0 °C, 12 h
intermediate structure
KI3
H2O
80% (2 steps)
intermediate structure
Ac2O
Pyr
RT, 15 min, 100%
intermediate structure
AIBN, n-Bu3SnH
PhH
RT, , 99%
intermediate structure
BBr3
CH2Cl2
0 °C, , 90%
intermediate structure
CrO3.2Pyr
CH2Cl2
0 °C
intermediate structure + intermediate structure
NaH
DME
RT, 60 min, 70% (2 steps)
intermediate structure
Zn(BH4)2
DME
RT, 30 min, 49%
"Also isolated was the C15-epimer (49 % yield)."
intermediate structure
K2CO3
MeOH
RT, 15 min, 100%
intermediate structure
3,4-Dihydropyran, TsOH
THF
RT, 15 min
intermediate structure
i-Bu2AlH
PhMe
-60 °C, 30 min
intermediate structure + intermediate structure
Dimsyl sodium
DMSO
80% (3 steps)
See the Wittig Reaction
intermediate structure
AcOH
H2O
37 °C, 3 h, 90%
intermediate structure