Synthesis of Prostaglandin F2α

Structure of Prostaglandin F2α

C20H34O5

Principal investigatorRobert B. Woodward
Publication year1973
Synthesis typeFormal
Number of steps 14 (linear)
References
Part 1 of 1
intermediate structure
Amberlyst 15, Glyoxylic acid monohydrate
DME
Reflux, , 55%
intermediate structure
NaBH4
MeOH
RT, 2 h, 97%
intermediate structure
MsCl
Pyr
-20 °C, , 97%
intermediate structure
KOH
i-PrOH
Reflux, , 89%
intermediate structure
K2CO3
DME, H2O
Reflux, 18 h, 70%
intermediate structure
Et3N, MsCl
CH2Cl2
0 °C, , 95%
intermediate structure
KOH
i-PrOH
Reflux, 2 h, 93%
intermediate structure
H2O2, KHCO3, PhCN
H2O, MeOH
RT, , 62%
"Also isolated was the epoxide diastereoisomer (25 % yield)."
intermediate structure
NH3
H2O
100 °C, 2 h, 90%
intermediate structure
HCl
MeOH
RT, , 99%
intermediate structure
NaNO2, NaOAc
AcOH
0 °C, , 80%
intermediate structure + intermediate structure
DME
Reflux, , 79%
See the Wittig Reaction
intermediate structure
Zn(BH4)2
Et2O
-18 °C, , 45%
"Also isolated was the C15-epimer (45 % yield)."
intermediate structure
Remaining...
(2 steps)
"See : Tetrahedron Lett., 1970, 11, 311."
intermediate structure