Synthesis and spectroscopic studies of furan-bridged polyazamacrocycles through 15,16-bis((prop-2-ynylamino)methyl)labdatriene transformations

Olga I. Brusentzeva, Yurii V. Kharitonov, Dmitry S. Fadeev, Elvira E. Shults

    Research output: Contribution to journalArticlepeer-review

    2 Citations (Scopus)

    Abstract

    Abstract: The design and the preparation of a small library of optically active polyazamacrocyclic compounds with a furan bridge, connected by (4-(methylaminomethyl)-1,2,3-triazole) rings with methylene, ethyloxyethyl or ethylethoxyethyl units from natural labdanoid lambertianic acid is reported. The synthesis of the key 15,16-bis((tert-butoxycarbonyl(prop-2-ynyl)amino)methyl)labda-8(9),13,15-labdatriene from the plant diterpenoid lambertianic acid is also described. CuAAC reaction of this compounds with various diazides in the presence of Cu(II)/sodium ascorbate in methylene chloride/water reaction medium led to the mentioned chiral macrocyclic compounds with a furan bridge binding Zn2+ ions in solution. Graphic abstract: [Figure not available: see fulltext.].

    Original languageEnglish
    Pages (from-to)245-250
    Number of pages6
    JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
    Volume96
    Issue number3-4
    DOIs
    Publication statusPublished - 1 Apr 2020

    Keywords

    • CuAAC reaction
    • Diazides
    • Diterpenoids
    • Furanolabdanoid dialkynes
    • Macroheterocycles
    • Zinc ion
    • ISOSTEVIOL
    • ACIDS
    • COMPLEXES
    • ENANTIOMERIC RECOGNITION
    • CYCLOADDITION
    • MACROCYCLIC FURANOLABDANOIDS
    • DERIVATIVES
    • MACROHETEROCYCLIC COMPOUNDS

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