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Named reactions

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Search synthesis

Prostaglandin F2α

Chemical structure of Prostaglandin_F2a
C20H34O5
Author Robert B. Woodward
Publication year 1973
Synthesis type Formal synthesis
Number of steps 15 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
Glyoxylic acid monohydrate, Amberlyst ® 15
DME
Reflux, 55 %
Chemical structure
NaBH4
MeOH
RT, 2 h, 97 %
Chemical structure
MsCl
Pyr
-20 °C, 97 %
Chemical structure
KOH
i-PrOH
Reflux, 89 %
Chemical structure
K2CO3
DME, H2O
Reflux, 18 h, 70 %
Chemical structure
MsCl, Et3N
CH2Cl2
0 °C, 95 %
Chemical structure
KOH
i-PrOH
Reflux, 2 h, 93 %
Chemical structure
H2O2, PhCN, KHCO3
MeOH, H2O
RT, 62 %

See the Payne Epoxidation
Also isolated was the epoxide diastereoisomer (25 % yield).
Chemical structure
NH3
H2O
100 °C, 2 h, 90 %
Chemical structure
HCl
MeOH
RT, 99 %
Chemical structure
NaNO2, NaOAc
AcOH
0 °C, 80 %

See the Tiffeneau-Demjanov Rearrangement
Chemical structure
+
Chemical structure
DME
Reflux, 79 %

See the Wittig Reaction
Chemical structure
Zn(BH4)2
Et2O
-18 °C, 45 %

Also isolated was the C15-epimer (45 % yield).
Chemical structure

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(2 steps)

See : Tetrahedron Lett., 1970, 11, 311.
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