A novel synthesis of racemic and enantiomeric forms of prostaglandin B1 methyl ester.
3-(Dimethoxyphosphorylmethyl)cyclopent-2-enone was converted into (+/-)-prostaglandin B1 methyl ester in two steps involving regioselective alkylation at C(2) with methyl 7-iodoheptanoate and subsequent Horner-Wittig reaction with dimer of 2-hydroxyheptanal (42% overall yield). The use of (R)- and (S)-2-(tert-butyldimethylsilyloxy)heptanal for the Horner olefination reaction gave, after deprotection of the hydroxy group, the enantiopure forms of the title compound in 28% overall yield.
Mikołajczyk
M
M
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Lódź, Sienkiewicza. marmikol@bilbo.cbmm.lodz.pl
Mikina
M
M
Jankowiak
A
A
D004952:Esters / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D011456:Prostaglandins B / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004952:Esters; D011456:Prostaglandins B; C034467:prostaglandin B1