Synthesis of Prostaglandin F2α

Structure of Prostaglandin F2α

C20H34O5

Principal investigatorRobert B. Woodward
Publication year1973
Synthesis typeFormal
Number of steps 14 (linear)
References
J. Am. Chem. Soc. 1973, 95, 6853.
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
MsCl, Et3N
CH2Cl2
0 °C, 95%
intermediate structure
KOH
i-PrOH
Reflux, 2 h, 93%
intermediate structure
PhCN, KHCO3, H2O2
H2O, MeOH
RT, 62%
See the Payne Epoxidation
"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
NaOAc, NaNO2
AcOH
0 °C, 80%
See the Tiffeneau-Demjanov Rearrangement
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
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Remaining...
(2 steps)
"See : Tetrahedron Lett., 1970, 11, 311."
intermediate structure