30890-35-8Relevant academic research and scientific papers
Biomimetic synthesis: Discovery of xanthanolide dimers
Shang, Hai,Liu, Junhua,Bao, Ruiyang,Cao, Yu,Zhao, Kun,Xiao, Chengqian,Zhou, Bing,Hu, Lihong,Tang, Yefeng
supporting information, p. 14494 - 14498 (2015/02/19)
Starting from xanthatin, the biomimetic synthesis of 4b,5b-epoxyxanthatin-1a,4a-endoperoxide, a novel monomeric xanthanolide, has been achieved. Moreover, four unprecedented xanthanolide dimers were synthesized by three different dimerizations of xanthatin, either in a head-tohead or head-to-tail fashion. Notably, these dimeric compounds were firstly identified as artifacts in the laboratory, and two of them, mogolides A and B, proved to be natural products present in the Xanthium mogolium Kitag plant.
Asymmetric total syntheses of xanthatin and 11,13-dihydroxanthatin using a stereocontrolled conjugate allylation to γ-butenolide
Matsumoto, Kenji,Koyachi, Kuniyoshi,Shindo, Mitsuru
, p. 1043 - 1049 (2013/02/23)
The stereocontrolled conjugate allylation to an optically pure γ-butenolide provided direct and reliable access to a trans-fused series of xanthanolide sesquiterpenoids and allowed for the enantioselective total syntheses of xanthatin and 11,13-dihydroxanthatin to be efficiently achieved.
Total synthesis of xanthanolides
Matsuo, Kazumasa,Ohtsuki, Keiko,Yoshikawa, Takashi,Shishido, Kozo,Yokotani-Tomita, Kaori,Shindo, Mitsuru
experimental part, p. 8407 - 8419 (2010/12/19)
The total synthesis and determination of the absolute configuration of (+)- and (-)-sundiversifolide have been achieved via intramolecular acylation and Wittig-lactonization as the key steps. The xanthanolide sesquiterpene lactones, 8-epi-xanthatin (1), d
Domino intramolecular enyne metathesis/cross metathesis approach to the xanthanolides. Enantioselective synthesis of (+)-8-epi-xanthatin
Kummer, David A.,Brenneman, Jehrod B.,Martin, Stephen F.
, p. 11437 - 11449 (2007/10/03)
The first total synthesis of (+)-8-epi-xanthatin (1) has been achieved in 14 steps starting from the commercially available ester 24, which was converted into aldehyde 23 in six steps. An enantioselective aldol reaction of 23 gave 30, which was transformed into triflate 22 in four steps, setting the stage for a palladium-catalyzed carbonylation reaction to form acrylate 34. Compound 34 was then subjected to a deprotection/lactonization sequence to furnish enyne 21, which underwent a domino enyne ring-closing metathesis/cross metathesis process to form a seven-membered carbocycle and (E)-conjugated dienone, thereby completing the synthesis of 1. This domino ruthenium-catalyzed metathesis reaction thus serves as an efficient method to construct the core of xanthanolide and other sesquiterpene lactones.
Application of a domino intramolecular enyne metathesis/cross metathesis reaction to the total synthesis of (+)-8-epi-xanthatin
Kummer, David A.,Brenneman, Jehrod B.,Martin, Stephen F.
, p. 4621 - 4623 (2007/10/03)
(Chemical Equation Presented) The first total synthesis of the novel sesquiterpene lactone (+)-8-epi-xanthatin (1) has been achieved starting from the commercially available ester 8. The synthesis features an asymmetric aldol reaction and palladium-catalyzed carbonylation/lactonization sequence leading to 4 and a domino ring-closing enyne metathesis/cross metathesis reaction to afford 1.
