Enantio- and stereospecific syntheses of 15(R)-Me-PGD2, a potent and selective DP2-receptor agonist
(Chemical Equation Presented) 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,Lee, Gue-Jae,Kim, Seongjin,Grant, Gail E.,Powell, William S.,Rokach, Joshua
supporting information; body text
p. 7213 - 7218
(2009/05/26)
Synthesis and Platelet Aggregation Inhibiting Activity of Prostaglandin D Analogues
Several prostaglandin D (PGD) analogues have been synthesized, incorpotating the following variations: (a) varying degrees of side-chain unsaturation, (b) C-9 hydroxy removed or in the unnatural 9β configuration, (c) metabolically stabilized analogues (e.
Bundy, Gordon L.,Morton, D. R.,Peterson, D. C.,Nishizawa, E. E.,Miller, W. L.
p. 790 - 799
(2007/10/02)
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