First Synthesis of Macrocyclic Furanolabdanoids via Cycloaddition of Diacetylenic Derivatives of Lambertianic Acid to 1,5-Diazidopentane

摘要

The catalytic 1,3-dipolar cycloaddition of azides to terminal alkynes (the Huisgen reaction) is related to a group of reactions that proceed with high yields, are simple to accomplish, and provide high regioselectiv-ity. Supplementary 1,2,3-triazole fragments introduced by this reaction impart a number of valuable properties to compounds (high chemical stability, possibility of hydrogen bonding, ability of these substitu-ents to behave as a linker and a coordinating group for cations and anions) [1, 2]. Copper-catalyzed 1,3-dipolar dialkyne—diazide cycloaddition is an efficient method for the synthesis of macrocyclic compounds with different sizes of inner cavity that differ in the spatial arrangement, number, and type of binding centers [3, 4]. In recent time, many publications deal with the use of natural compounds—steroids [5, 6], triterpenoids [7], and cyclic peptides [8]—as the main building blocks in the synthesis of macrocyclic compounds.