Undec-10-enal in the Synthesis of Undec-10-enyl Undec-10-enoate and O- and N-containing Macroheterocycles

Abstract

An effective synthesis of four potentially biologically active O- and N-containing 23-, 28-, 30-, and 31-membered macroheterocycles from undec-10-enal was carried out. First, undec-10-enal was converted to undec-10-enyl undec-10-enoate via the Tishchenko disproportionation reaction catalyzed by Al(i-PrO)₃. The subsequent Wacker–Tsuji oxidation of undec-10-enyl undec-10-enoate gave 10-oxoundecanyl 10-oxoundecanoate. Finally, the [1+1]-condensation of 10-oxoundecanyl-10-oxoundecenoate with hydrazine hydrate or malonic, glutaric, or adipic acid dihydrazides resulted in the synthesis of four macroheterocycles.