M. V. Zlokazov

Enantiosective synthesis of a substituted cyclopentanone with all-carbon quaternary stereocenter

The enantioselective synthesis of a substituted cyclopentanone with an all-carbon quaternary stereocenter was performed using an asymmetric nitroaldol condensation involving metal-complex catalysis and stereocontrolled silyl nitronate intramolecular [3+2] cycloaddition reaction in the key steps of the synthesis.

New chiral CuII complexes and their catalytic activity in enantioselective Henry reaction

New chiral polydentante ligands capable of complexation of Cu2+ ions were synthesized using readily available derivatives of (S)-proline, d-glyceraldehyde, and imidazole as the starting materials. The synthesized complexes are efficient catalysts for enantioselective nitroaldol condensation (the Henry reaction).

Annulation of unsaturated silyl nitronates

The intramolecular dipolar [3+2]-cycloaddition of acyclic δ,ɛ- and ɛ, ζ-unsaturated silyl nitronates was used in the stereoselective synthesis of functionalized cyclopentanone and cyclohexanone, respectively. The reaction with the γ,δ-unsaturated analog did not afford the corresponding cyclobutanone.

New synthesis of (5S*,7aS*)-5-benzyloxy-5,6,7,7a-tetrahydrocyclopenta[c]pyran-3(1H)-one

To increase the efficiency of the recently suggested total synthesis of iso- and neuroprostanes, a possibility of transformation of its side products, i.e., syn- and anti-2-[(2S*,5S*)-2-benzyloxy-5-hydroxymethyl-Z-cyclopentylidene]ethanaldoximes, to (5S*,7aS*)-5-benzyloxy-5,6,7,7a-tetrahydrocyclopenta[c]pyran-3(1H)-one was studied.