58687-40-4Relevant academic research and scientific papers
Synthesis of Biologically Active Analogue of Prostaglandin E2 (Racemate and Enantiomerically Pure Compounds)
Bartmann, Wilhelm,Beck, Gerhard,Jaehne, Gerhard,Lerch, Ulrich,Wess, Guenther
, p. 321 - 326 (2007/10/02)
Transformation of 6-chloro-3-oxo-2-oxabicyclooctane-8-carbaldehyde (6) by an eight-step synthesis leads to racemic (5Z,13E)-11,15-dihydroxy-16,16-dimethyl-9-oxo-18-oxa-5,13-prostadienoic acid (1) (dimoxaprost).The synthesis starts with the introduction of the ω-side chain of 1 into 6 by Horner-Emmons-Wittig reaction with the phosphonate 7.Ring cleavage and rearrangement of 8 affords enone 9a with unprotected hydroxyl group.By stereoselective reduction of 9a, diol 11a is obtained.Subsequently, 11a is converted in five steps through the "Corey synthesis into 1.The 5-ketoprostacyclin 17 is isolated as byproduct of the Jones oxidation of 15.Finally, the synthesis of optically pure (-)-1 and (+)-1, starting with the keto acids (+)-2 and (-)-2, is described.
