Enantio-and Stereospecific Syntheses of 15 (R)-Me-PGD2, A Potent and Selective DP2− Receptor Agonist

…, S Kim, GE Grant, WS Powell, J Rokach

Index: Patel, Pranav; Lee, Gue-Jae; Kim, Seongjin; Grant, Gail E.; Powell, William S.; Rokach, Joshua Journal of Organic Chemistry, 2008 , vol. 73, # 18 p. 7213 - 7218

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Citation Number: 9

Abstract

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 15 R-methyl prostaglandin D2 and allows rapid access to other ...