Synthesis of Prostaglandin F2α
C20H34O5
Principal investigator | Robert B. Woodward |
---|---|
Publication year | 1973 |
Synthesis type | Formal |
Number of steps | 14 (linear) |
References |
Part 1 of 1
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Amberlyst 15,
Glyoxylic acid monohydrate
DME
Reflux, 55%
NaBH4
MeOH
RT, 2 h, 97%
MsCl
Pyr
-20 °C, 97%
KOH
i-PrOH
Reflux, 89%
K2CO3
DME, H2O
Reflux, 18 h, 70%
MsCl,
Et3N
CH2Cl2
0 °C, 95%
KOH
i-PrOH
Reflux, 2 h, 93%
PhCN,
KHCO3,
H2O2
H2O, MeOH
RT, 62%
See the Payne Epoxidation
"Also isolated was the epoxide diastereoisomer (25 % yield)."
NH3
H2O
100 °C, 2 h, 90%
HCl
MeOH
RT, 99%
Zn(BH4)2
Et2O
-18 °C, 45%
"Also isolated was the C15-epimer (45 % yield)."
Remaining...
(2 steps)
"See : Tetrahedron Lett., 1970, 11, 311."