Synthetic transformations of higher terpenoids: XXXVI. Synthesis of furanolabdanoid glycoconjugates with a 1,2,3-triazole linker

Synthetic transformations of higher terpenoids: XXXVI. Synthesis of furanolabdanoid glycoconjugates with a 1,2,3-triazole linker

Procedures have been developed for the synthesis of 16-[(propargyloxy)methyl]- and 7- and 18-(propargyloxy)labda-8(9),13,14-trienes from phlomisoic acid. Copper-catalyzed cycloaddition of the labdanoid alkynes to azido derivatives of α-D-glucose, D-galactose, D-xylose, and L-arabinose afforded the c...

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Bibliographic Details
Published in:Russian journal of organic chemistry Vol. 53; no. 1; pp. 35 - 46
Main Authors: Kremenko, O. I., Kharitonov, Yu. V., Shul’ts, E. E.
Format: Journal Article
Language:English
Published: Moscow Pleiades Publishing 2017
Springer Nature B.V
Subjects:
Alkynes
Arabinose
Chemistry
Chemistry and Materials Science
Cycloaddition
Galactose
Organic Chemistry
Synthesis
Terpenes
Triazoles
Trienes
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Summary:Procedures have been developed for the synthesis of 16-[(propargyloxy)methyl]- and 7- and 18-(propargyloxy)labda-8(9),13,14-trienes from phlomisoic acid. Copper-catalyzed cycloaddition of the labdanoid alkynes to azido derivatives of α-D-glucose, D-galactose, D-xylose, and L-arabinose afforded the corresponding N -glycosyl-1,2,3-triazole conjugates.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428017010079