Semeno V. Synthesis of saturated bicyclic derivatives using electrophilic double bond functionalization and subsequent intramolecular alkylation

The dissertation work is devoted to the study of novel approaches for the synthesis of di–substituted bicyclic compounds. The developed procedure involves the use of monocyclic alkene carboxylates as starting compounds for the synthesis and application of a sequence of reactions involving double bond functionalization, and further nucleophilic intramolecular alkylation. An approach for the synthesis of 1,3–disubstituted bicyclo[2.1.0]pentanes was described. The method was based on the use of LiHMDS in intramolecular cyclization of trisubstituted cyclopentanecarboxylates bearing a leaving group at C–4 position and an additional substituent at C–3 position. The developed synthetic procedure results in both cis– and trans–1,3– disubstituted bicyclo[2.1.0]pentane carboxylic acids, obtained in diastereoselective manner on a scale up to 80 g of the final product.