Synthesis of Prostaglandin F2α
C20H34O5
Principal investigator | Elias J. Corey |
---|---|
Publication year | 1969 |
Synthesis type | Total |
Number of steps | 17 (linear) |
References |
Part 1 of 1
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MeOCH2Cl,
NaH
THF
-55 °C
KOH
DMSO
30 °C, 14 h, 80% (3 steps)
NaOH
H2O
0 °C, 12 h
KI3
H2O
80% (2 steps)
Ac2O
Pyr
RT, 15 min, 100%
n-Bu3SnH,
AIBN
PhH
RT, 99%
BBr3
CH2Cl2
0 °C, 90%
Zn(BH4)2
DME
RT, 30 min, 49%
"Also isolated was the C15-epimer (49 % yield)."
K2CO3
MeOH
RT, 15 min, 100%
3,4-Dihydropyran,
TsOH
THF
RT, 15 min
i-Bu2AlH
PhMe
-60 °C, 30 min
AcOH
H2O
37 °C, 3 h, 90%