Synthetic Transformations of Sesquiterpene Lactones 10*. Synthesis of 13-Arylguaianolides

Synthetic Transformations of Sesquiterpene Lactones 10*. Synthesis of 13-Arylguaianolides Full article

Journal

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

Output data

Year: 2016, Volume: 52, Number: 10, Pages: 788-796 Pages count : DOI: 10.1007/s10593-016-1967-7

Tags

arglabin; grosheimin; guaianolides; ludartin sesquiterpenoids; Heck reaction; X-ray structural analysis

Authors

Kihkentayeva Anarkul S. ¹ , Shults Elvira E. ^2,3 , Gatilov Yurii V. ^2,3 , Patrushev Sergey S. ^2,3 , Karim Sultan ¹ , Atazhanova Gayane A. ¹ , Adekenov Sergazy M. ¹

Affiliations

1	(Данные Web of science) JSC Int Res & Prod Holding Phytochem, 4 M Gazaliev St, Karaganda 100009, Kazakhstan
2	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Lavrentieva Ave, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk Natl Res State Univ, 2 Pirogova St, Novosibirsk 630090, Russia

The Heck reaction of methylidene lactones of guaiane type, arglabin and ludartin, with aryl halides occurs with the formation of the respective (E)- and (Z)-13-arylidene-substituted derivatives and the respective endocyclic isomer, the ratio of which depends on the nature of methylidenelactone and the reaction conditions. The arylation of ludartin occurred with a lower yield of the target products and was accompanied by the formation of chamazulene. The interaction of grosheimin with aryl halides under Heck reaction led to the exocyclic products with (E)- and (Z)-configuration, with the latter as the major isomers. The structure of two compounds was established by X-ray structural analysis.

Kihkentayeva A.S. , Shults E.E. , Gatilov Y.V. , Patrushev S.S. , Karim S. , Atazhanova G.A. , Adekenov S.M.
Synthetic Transformations of Sesquiterpene Lactones 10*. Synthesis of 13-Arylguaianolides
Chemistry of Heterocyclic Compounds. 2016. V.52. N10. P.788-796. DOI: 10.1007/s10593-016-1967-7 WOS Scopus РИНЦ

Published print:	Oct 1, 2016
Published online:	Nov 23, 2016

Web of science	WOS:000389407100008
Scopus	2-s2.0-85047194963
Elibrary	35480542
OpenAlex	W2554146897