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

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

Journal

Journal of Inclusion Phenomena and Macrocyclic Chemistry
ISSN: 0923-0750 , E-ISSN: 1573-1111

Output data

Year: 2020, Volume: 96, Number: 3-4, Pages: 245-250 Pages count : 6 DOI: 10.1007/s10847-019-00965-z

Tags

Macroheterocycles; Diterpenoids; Furanolabdanoid dialkynes; Diazides; CuAAC reaction; Zinc ion

Authors

Brusentzeva Olga, I ¹ , Kharitonov Yurii, V ¹ , Fadeev Dmitry S. ¹ , Shults Elvira E. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Novosibirsk Inst Organ Chem, Siberian Branch, Lab Med Chem, Lavrentyev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova St 2, Novosibirsk 630090, Russia

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. [GRAPHICS]

Brusentzeva O.I. , Kharitonov Y.V. , Fadeev D.S. , Shults E.E.
Synthesis and spectroscopic studies of furan-bridged polyazamacrocycles through 15,16-bis((prop-2-ynylamino)methyl)labdatriene transformations
Journal of Inclusion Phenomena and Macrocyclic Chemistry. 2020. V.96. N3-4. P.245-250. DOI: 10.1007/s10847-019-00965-z WOS Scopus

Published online:	Nov 22, 2019
Published print:	Apr 1, 2020

Web of science	WOS:000498020800001
Scopus	2-s2.0-85075348240
OpenAlex	W2990704197