Heteroanalogs of ascidian alkaloids have been synthesized, and for the first time 10 different types of saturated carbo- and heteroannulated pyridones have been obtained. A new method for the formation of decahydro[1,3]oxazolo[2,3-j]quinoline and octahydro-5H-cyclopenta[b][1,3]oxazolo[3,2-a]pyridine was proposed. The synthesis of these heterocycles is based on the three-component cyclization of trifluoroacetoacetic ester and cycloketones with 1,2- and 1,3-dinucleophiles. It was found that reactions with amino alcohols are distinguished by the possibility of isolating carbocyclopyridones of various degrees of saturation. The diastereomeric structure of the synthesized heterocycles has been studied, and the mechanism of their formation has been proposed. Antitumor, anti-influenza and analgesic agents have been found among the synthesized compounds.