Enantio- and Stereospecific Syntheses of 15(R)-Me-PGD2, A Potent and Selective DP2−Receptor Agonist
| Autor: | Joshua Rokach, Gail E. Grant, Pranav Patel, William S. Powell, Gue-Jae Lee, Seongjin Kim |
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| Rok vydání: | 2008 |
| Předmět: |
Time Factors
Prostaglandin D2 Chemistry Stereochemistry Receptors Prostaglandin Organic Chemistry Synthon Molecular Conformation Enantioselective synthesis Total synthesis Stereoisomerism Metathesis Chemical synthesis Rats Stereocenter Structure-Activity Relationship Stereospecificity Salt metathesis reaction Animals Receptors Immunologic Chromatography High Pressure Liquid |
| Zdroj: | The Journal of Organic Chemistry. 73:7213-7218 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo801190m |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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