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

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Synthesis and spectroscopic studies of furan-bridged polyazamacrocycles through 15,16-bis((prop-2-ynylamino)methyl)labdatriene transformations. / Brusentzeva, Olga I.; Kharitonov, Yurii V.; Fadeev, Dmitry S. et al.

In: Journal of Inclusion Phenomena and Macrocyclic Chemistry, Vol. 96, No. 3-4, 01.04.2020, p. 245-250.

Research output: Contribution to journal › Article › peer-review

Harvard

Brusentzeva, OI, Kharitonov, YV, Fadeev, DS & Shults, EE 2020, '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, vol. 96, no. 3-4, pp. 245-250. https://doi.org/10.1007/s10847-019-00965-z

APA

Brusentzeva, O. I., Kharitonov, Y. V., Fadeev, D. S., & Shults, E. E. (2020). 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, 96(3-4), 245-250. https://doi.org/10.1007/s10847-019-00965-z

Vancouver

Brusentzeva OI, Kharitonov YV, Fadeev DS, Shults EE. 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 Apr 1;96(3-4):245-250. doi: 10.1007/s10847-019-00965-z

Author

Brusentzeva, Olga I. ; Kharitonov, Yurii V. ; Fadeev, Dmitry S. et al. / Synthesis and spectroscopic studies of furan-bridged polyazamacrocycles through 15,16-bis((prop-2-ynylamino)methyl)labdatriene transformations. In: Journal of Inclusion Phenomena and Macrocyclic Chemistry. 2020 ; Vol. 96, No. 3-4. pp. 245-250.

BibTeX

@article{ce132484b0b04008a7f22a15e7a7477f,

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

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.",

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

author = "Brusentzeva, {Olga I.} and Kharitonov, {Yurii V.} and Fadeev, {Dmitry S.} and Shults, {Elvira E.}",

year = "2020",

month = apr,

day = "1",

doi = "10.1007/s10847-019-00965-z",

language = "English",

volume = "96",

pages = "245--250",

journal = "Journal of Inclusion Phenomena and Macrocyclic Chemistry",

issn = "0923-0750",

publisher = "Springer Netherlands",

number = "3-4",

}

RIS

TY - JOUR

T1 - Synthesis and spectroscopic studies of furan-bridged polyazamacrocycles through 15,16-bis((prop-2-ynylamino)methyl)labdatriene transformations

AU - Brusentzeva, Olga I.

AU - Kharitonov, Yurii V.

AU - Fadeev, Dmitry S.

AU - Shults, Elvira E.

PY - 2020/4/1

Y1 - 2020/4/1

N2 - 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.

AB - 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.

KW - CuAAC reaction

KW - Diazides

KW - Diterpenoids

KW - Furanolabdanoid dialkynes

KW - Macroheterocycles

KW - Zinc ion

KW - ISOSTEVIOL

KW - ACIDS

KW - COMPLEXES

KW - ENANTIOMERIC RECOGNITION

KW - CYCLOADDITION

KW - MACROCYCLIC FURANOLABDANOIDS

KW - DERIVATIVES

KW - MACROHETEROCYCLIC COMPOUNDS

UR - http://www.scopus.com/inward/record.url?scp=85075348240&partnerID=8YFLogxK

U2 - 10.1007/s10847-019-00965-z

DO - 10.1007/s10847-019-00965-z

M3 - Article

AN - SCOPUS:85075348240

VL - 96

SP - 245

EP - 250

JO - Journal of Inclusion Phenomena and Macrocyclic Chemistry

JF - Journal of Inclusion Phenomena and Macrocyclic Chemistry

SN - 0923-0750

IS - 3-4

ER -

ID: 22407914