Synthetic transformations of sesquiterpene lactones 9.(*) Synthesis of 13-(pyridinyl)eudesmanolides

Synthetic transformations of sesquiterpene lactones 9.(*) Synthesis of 13-(pyridinyl)eudesmanolides Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Output data

Year: 2016, Volume: 52, Number: 3, Pages: 165-171 Pages count : 7 DOI: 10.1007/s10593-016-1855-1

Tags

bromopyridines; iodopyridines; isoalantolactone; Heck reaction

Authors

Patrushev Sergey S. ^1,2 , Shakirov Makhmut M. ¹ , Shults Elvira E. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Akad Lavrentieva Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, 2 Pirogova St, Novosibirsk 630090, Russia

The reaction of isoalantolactone, a sesquiterpene alpha-methylidene-gamma-lactone, with bromo(iodo)pyridines under the Heck reaction conditions gave 3-(pyridylmethylidene)-8D degrees-methyldecahydronaphtho[2,3-b]furan-2(3De)-ones and 3-(pyridylmethyl)-8D degrees-methyloctahydronaphtho[2,3-b]-furan-2(4De)-ones, products of double bond migration. The yield and product ratio depended on the reaction conditions and the nature of halopyridine. The effectiveness of Pd(OAc)2-caffeine catalytic system was demonstrated in this reaction.

Patrushev S.S. , Shakirov M.M. , Shults E.E.
Synthetic transformations of sesquiterpene lactones 9.(*) Synthesis of 13-(pyridinyl)eudesmanolides
Chemistry of Heterocyclic Compounds. 2016. V.52. N3. P.165-171. DOI: 10.1007/s10593-016-1855-1 WOS Scopus РИНЦ OpenAlex

Published print:	Mar 1, 2016
Published online:	Apr 27, 2016

Web of science:	WOS:000376466200008
Scopus:	2-s2.0-84978999490
Elibrary:	27091503
OpenAlex:	W2461582573

DB	Citing
Web of science	13
Scopus	10
Elibrary	11
OpenAlex	14