Synthesis from Undecylenic Acid of Macroheterocycles with Diacylhydrazine and Ester Fragments
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A three-step synthesis of potentially biologically active 30- and 32-membered macroheterocycles with esters and acylhydrazines starting from methyl undecylenate was developed based on [1+1]-condensation of intermediate tetraesters, i.e., bis(10′ -methoxy-10′-oxodecyl)- or bis(11′-methoxy-11′ -oxoundecyl)hexanedioate, with hydrazine hydrate. The structures of the synthesized compounds were confirmed using IR and NMR spectroscopy and mass spectrometry.
Keywordsundecylenic acid ozonolysis hydroboration-oxidation [2+1]-condensation [1+1]-condensation macroheterocycles synthesis
The work was financially supported by RAS program “Basic Principles of Chemistry” on topic No. 8 “Chemo-, regio-, and stereoselective transformations of terpenoids, steroids, and lipids for targeted synthesis of low-molecular-mass bioregulators” (State Reg. No. AAAA-A17-117011910023-2, 2017).
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