ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
stereochemistry stereochemistry (general, optical resolution) O 0030
-051Asymmetric Synthesis of Isocarbacyclin Based on the Olefination-Isomerization-Coupling Process with Chiral Sulfoximines.-Key steps in the synthesis of the title compound (XV) are an asymmetric olefination using the chiral sulfoximine (II) to furnish (III) followed by isomerization and cross-coupling reaction to afford alkene (VI) and the asymmetric deprotonation-alkylation of key intermediate (VII). The palladium-catalyzed allylic rearrangement of compound (XIII) to (XIV) furnishes an equilibrium mixture of the rearranged product and the educt in contrast to reports on unidirectional Pd-catalyzed rearrangements of analogous monocyclic acetates. Isocarbacyclin (XV), which is investigated for clinical application in myocardial infarction, cerebrovascular disorder and chronical arterial obstruction, is contaminated with 5% of the isomeric acid resulting from acetate (XIII) and can be obtained pure in 33% yield (from XIV) after recrystallization. -(BUND, J.; GAIS, H.-J.; SCHMITZ, E.; ERDELMEIER, I.; RAABE, G.; Eur. J.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.