618387-07-8Relevant articles and documents
Enantio- and stereospecific syntheses of 15(R)-Me-PGD2, a potent and selective DP2-receptor agonist
Patel, Pranav,Lee, Gue-Jae,Kim, Seongjin,Grant, Gail E.,Powell, William S.,Rokach, Joshua
experimental part, p. 7213 - 7218 (2009/05/26)
(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.
A short multigram asymmetric synthesis of prostanoid scaffolds
Depré, Dominique,Chen, Lian-Yong,Ghosez, Léon
, p. 6797 - 6812 (2007/10/03)
Enantiomerically pure polysubstituted cyclopentanes which can be regarded as prostanoid scaffolds have been prepared by an efficient synthetic sequence readily applicable to the preparation of multigram quantities. The first key reaction is the diastereoselective allylmetallation of oxoamide 4 which is readily prepared from γ-butyrolactone and an enantiomerically pure 2,5-dimethylpyrrolidine. The second key-step is an intramolecular [2+2] cycloaddition of a keteneiminium salt leading to bicylo[3.2.0] heptanones. These intermediates have been easily transformed into a variety of prostanoid scaffolds of high enantiomeric purities.
