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Synthesis and spectroscopic studies of chiral macrocyclic furanolabdanoids connected on the 16,17-positions by 1,2,3-triazole rings with methylene or oxamethylene units Full article

Journal Journal of Inclusion Phenomena and Macrocyclic Chemistry
ISSN: 0923-0750 , E-ISSN: 1573-1111
Output data Year: 2016, Volume: 84, Number: 3-4, Pages: 197-202 Pages count : 6 DOI: 10.1007/s10847-016-0596-1
Tags Diterpenoids; Furanolabdanoid dialkynes; Diazides; CuAAC reaction; Mercury ion
Authors Kharitonov Yurii V. 1,2 , Shakirov Makhmut M. 1 , Shults Elvira E. 1,2
Affiliations
1 (Данные Web of science) Russian Acad Sci, Novosibirsk Organ Chem Inst, Med Chem Lab, Siberian Branch, Lavrentyev Ave 9, Novosibirsk 630090, Russia
2 (Данные Web of science) Novosibirsk State Univ, Dept Phys, Pirogova St 2, Novosibirsk 630090, Russia

Abstract: Derivatives of natural diterpenoid methyl lambertianate containing propargyloxy substituents in 16,17-positions were obtained. CuAAC reaction of methyl 17-propargyloxy-16-[(prop-2-yn-1-yloxy)methyl]labdadienoate with various diazides in the presence of Cu(II)/sodium ascorbate in methylene chloride/water reaction medium gave chiral macrocyclic compounds connected on the 16 and 17-positions by 1,2,3-triazole rings with methylene, ethyloxyethyl or ethylethoxyethyl units. The obtained macrocyclic structures showed high selectivity and affinity for Hg2+ ion by the 1,2,3-triazole rings.
Cite: Kharitonov Y.V. , Shakirov M.M. , Shults E.E.
Synthesis and spectroscopic studies of chiral macrocyclic furanolabdanoids connected on the 16,17-positions by 1,2,3-triazole rings with methylene or oxamethylene units
Journal of Inclusion Phenomena and Macrocyclic Chemistry. 2016. V.84. N3-4. P.197-202. DOI: 10.1007/s10847-016-0596-1 WOS Scopus
Dates:
Published online: Feb 1, 2016
Published print: Apr 1, 2016
Identifiers:
Web of science WOS:000371794500003
Scopus 2-s2.0-84963553937
OpenAlex W2298534508
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