Prostaglandin Nomenclature - The Stoltz Group

O
Me Me
Stork Enantiospecific Route From Glucose – 1978
O
1. NaOMe
OH
2. p-TsCl, pyr.
3. ethyl vinyl ether
H +
EEO
O
O
O
OEE
O
O
MeO 2C
O
Me Me
O
MeO
OMe
Me OMe
CH 3CH 2CO 2H
(80% yield)
O
O
O
Me
Me
O O
OMe
H
Stork, G. et al. J. Am. Chem. Soc. 1978, 100, 8272–8273.
Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis; VCH: Weinheim, 1966: pp 144–151.
OEE
OTs
1.
2.
n-Bu 2CuLi (10 equiv)
Et 2O, -40°C
H 2SO 4(aq),
THF, 25 °C
(35% yield, 5 steps)
HO
O
O
O
Me Me
OH
O
HO
MeO 2C
C 5H 11
HO
OH
PGF 2α
O
O
O
ethyl vinyl ether, H +
CO 2H
Me
LHMDS, THF, -78°C
then
Br 4OTBDPS
THF/HMPA, -40→ -20 °C
(71% yield)
OH
OTBDPS 1. DIBAL
2. HCN, EtOH
NC
OTBDPS
3. 50% AcOH, THF, 35 °C
4. p-TsCl, pyr.
(37% yield)
TsO
OH
OH