Synthesis of Prostaglandin F2α

Structure of Prostaglandin F2α

C20H34O5

Principal investigator	Elias J. Corey
Publication year	1969
Synthesis type	Total
Number of steps	17 (linear)
References	J. Am. Chem. Soc. 1969, 91, 5675.

Part 1 of 1

intermediate structure

MeOCH2Cl, NaH

THF

-55 °C

intermediate structure

2-Chloroacrylonitrile, Cu(BF4)2

0 °C

See the Diels-Alder Reaction

intermediate structure

KOH

DMSO

30 °C, 14 h, 80% (3 steps)

intermediate structure

mCPBA

CH2Cl2

95%

See the Baeyer-Villiger Oxidation

intermediate structure

NaOH

H2O

0 °C, 12 h

intermediate structure

KI3

H2O

80% (2 steps)

intermediate structure

Ac2O

Pyr

RT, 15 min, 100%

intermediate structure

n-Bu3SnH, AIBN

PhH

RT, 99%

intermediate structure

BBr3

CH2Cl2

0 °C, 90%

intermediate structure

CrO3.2Pyr

CH2Cl2

0 °C

See the Sarett Oxidation

intermediate structure

+

intermediate structure

NaH

DME

RT, 60 min, 70% (2 steps)

See the Horner-Wadsworth-Emmons Reaction

intermediate structure

Zn(BH4)2

DME

RT, 30 min, 49%

"Also isolated was the C15-epimer (49 % yield)."

intermediate structure

K2CO3

MeOH

RT, 15 min, 100%

intermediate structure

3,4-Dihydropyran, TsOH

THF

RT, 15 min

intermediate structure

i-Bu2AlH

PhMe

-60 °C, 30 min

intermediate structure

+

intermediate structure

Dimsyl sodium

DMSO

80% (3 steps)

See the Wittig Reaction

intermediate structure

AcOH

H2O

37 °C, 3 h, 90%

intermediate structure

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