ИСТИНА

containing pyrroliding ring1. Various natural products and biologically active compounds were synthesized during past years2. Also many biologically relevant compounds, such as hexahydroindoles and octahydropyrroles can be prepared in streoselective fashion3. For this and others cycloalkano[b]fused pyrrolidines two types of ring junction are possible. Since preparation of cis- fused compound is well known, we aimed to create an approach to trans-fused heterocycles. In our present work we have developed enantio- and stereoselctive approach to the octahydrocyclohepta[b]pyrrol-4(1H)-one scaffold. The method based on Aza-Cope-Mannich rearrangement of trans-2-amino-2-ethenylcyclohexanols which resulted in only one of 4 possible diastereomers. The salient features of the route include asymmetric Shi epoxidation, epoxide opening and aza-Cope-Mannich reaction. Overall efficiency of this process allows us to prepare 100 g quantities of target compounds for subsequent modification and preparation of compound libraries for high- throughput screening. References: 1. Overman, L. E.; Humphreys, P. G.; Welmaker, G. S. Org. React. 2011, 75, 747. 2. Cooke, A.; Bennetta, J.; McDaid, E. Tetrahedron Letters 2002, 43, 903–905 3. Belov, D.S.; Lukyanenko, E. R.; Kurkin, A.V.; Yurovskaya, M. A.; Tetrahedron 2011, 67, 9214-9218.