Enantio- and stereospecific syntheses of 15(R)-Me-PGD2, a potent and selective DP2-receptor agonist.
The first total synthesis of 15(R)-Me-PGD2 3 is reported. The synthesis is based on the enantioselective and stereospecific syntheses of synthon 17 and its attachment to the five-membered ring by a olefin cross metathesis reaction. This approach permits the introduction of a side chain with a predetermined stereogenic center into the prostanoid ring, resulting in the synthesis of 15R-methyl prostaglandin D2 and allows rapid access to other prostanoids.
Patel
Pranav
P
Department of Chemistry, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901, USA.
Lee
Gue-Jae
GJ
Kim
Seongjin
S
Grant
Gail E
GE
Powell
William S
WS
Rokach
Joshua
J
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D008968:Molecular Conformation; D015230:Prostaglandin D2 / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology*; D051381:Rats; D011971:Receptors, Immunologic / Q000819:agonists*; D011982:Receptors, Prostaglandin / Q000819:agonists*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013997:Time Factors
C532725:15R-methyl prostaglandin D2; D011971:Receptors, Immunologic; D011982:Receptors, Prostaglandin; D015230:Prostaglandin D2; C036293:prostaglandin D2 receptor