1856-58-2Relevant academic research and scientific papers
Sesquiterpenolides from Inula racemosa and their chemical transformations
Kaur, Ramandeep,Chahal,Bhardwaj, Urvashi
, p. 568 - 570 (2017)
Inula racemosa roots are rich source of sesquiterpene lactones. Soxhlet extraction of roots using chloroform followed by column chromatography on silver nitrate impregnated silica gel led to the isolation of two sesquiterpene lactones namely alantolactone
Isolation, Chemical Transformation, and Antifungal Potential of Sesquiterpene Lactones from Inula Racemosa
Kaur, Ramandeep,Chahal,Urvashi
, p. 207 - 212 (2020/04/17)
The present study reports the isolation of two eudesmanolide type sesquiterpenoid lactones, viz. alantolactone and isoalantolactone, from the roots of Inula racemosa Hook L. and their chemical transformations using various reagents. All the compounds isol
Total Synthesis of Three Eudesman-12,8-olides, (+/-)-Isoalantolactone, (+/-)-Dihydrocallitrisin and (+/-)-Septuplinolide; Structure Revision of Septuplinolide
Tada, Masahiro,Yamada, Hirokazu,Kanamori, Akira,Chiba, Kazuhiro
, p. 239 - 248 (2007/10/02)
Four eudesman-12,8-olides, (+/-)-isoalantolactone, (+/-)-dihydrocallitrisin, (+/-)-septuplinolide and its epimeric eudesmanolide at C-4 were synthesized stereoselectively via the route involving alkylation annulation of 2-methyl-3-furoic acid and oxidation of the furan ring.It was found that the structure of septuplinolide is the C-4 epimer of the reported structure.
Synthesis of Deuterium-Labeled Sesquiterpene Lactones Isolated from Inula helenium L.
Schaeffer, Marcel,Stampf, Jean-Luc,Benezra, Claude
, p. 6106 - 6113 (2007/10/02)
Reduction of the vinyl sulfoxides 9 and 10 derived from isoalantolactone (1) and alantolactone (2) with NaBD4 yielded deuterium-labeled lactones 11 and 12.Amalgam reduction of sulfides 7 and 8 or sulfoxides 9 and 10 gave labeled products but not the expected deuterated lactones 11 and 12.Satisfactory deuteration of alantolactone 2 could be achieved by CF3COOD hydrolysis of (tributylstannyl)alantolactone (23) obtained in four steps from alantolactone 2.
TOTAL SYNTHESIS OF (+/-)-ISOALANTOLACTONE AND (+/-)-DIHYDROCALLITRISIN
Tada, Masahiro
, p. 441 - 444 (2007/10/02)
Two eudesmanolides having opposite stereochemistry of lactone ring each other, (+/-)-isoalantolactone and (+/-)-dihydrocallitrisin were sythesized stereoselectively by a route involving alkylation of 2-methyl-3-furonic acid and oxidation of furan ring.
An Annelation Approach to the Synthesis of Eudesmane and Elemane Sesquiterpene Lactones. Total Synthesis of dl-Dihydrocallitrisin, dl-7,8-Epialantolactone, dl-7,8-Epiisoalantolactone, and dl-Atractylon
Schultz, Arthur G.,Godfrey, Jollie D.
, p. 2414 - 2428 (2007/10/02)
An annelation approach to the synthesis of eudesmane sesquiterpenes is described.The 1,6-annelation reagent α-carbomethoxy-β-methyl-γ-methylidene-Δα,β-butenolide (1) is used to construct the linear tricyclic lactone 2,5,6,7,8,8a,9,9aβ-octahydro-8aβ-methyl-2-oxonaphthofuran-3-carboxylic acid methyl ester (2).The conversion of 2 to dl-dihydrocallitrisin (3), dl-7,8-epialantolactone (4), dl-7,8-epiisoalantolactone (5), and dl-atractylon (6) is detailed.Studies directed toward synthesis of the elemane sesquiterpene lactones vernomenin and vernolepin also are presented.
