73366-01-5Relevant academic research and scientific papers
Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps
Jagtap, Pratap R.,Císa?ová, Ivana,Jahn, Ullrich
supporting information, p. 750 - 755 (2018/02/09)
A very short three-step approach to trans,trans,trans-2,5-diaryl-3,4-dimethyltetrahydrofuran lignans is reported. The carbon skeleton is assembled in a single step based on an unprecedented tandem reaction consisting of 1,2-addition of aryllithium reagents to α,β-unsaturated aldehydes, ruthenium-catalyzed redox isomerization of the resulting alkoxides to enolates and their dimerization triggered by single electron oxidation. The resulting 2,3-dialkyl-1,4-diketones form with moderate to good d/l-diastereoselectivity and are transformed to the target tetrahydrofuran lignans by reduction and diastereoselective cycloetherification.
Aryltetralols from Holostylis reniformis and syntheses of lignan analogous
Pereira, Marcos D.P.,Ferreira, Matheus R.,Messiano, Gisele B.,Cerávolo, Isabela Penna,Lopes, Lucia M.X.,Krettli, Antoniana U.
, p. 200 - 205 (2015/06/30)
Abstract Two new lignans, an aryltetralol and its methyl ether analogous, were isolated from Holostylis reniformis (Aristolochiaceae) together with futokadsurin C and (-)-8′-epi-aristoligone. The latter was also obtained as an enantiomeric mixture by synt
Total synthesis of cyclogalgravin and its dicarboxyl analog using sc(otf)3-mediated highly diastereoselective ring expansion of 1-(arylhydroxymethyl)cyclopropanecarboxylates
Sakuma, Daichi,Ito, Junki,Sakai, Ryo,Taguchi, Ryota,Nishii, Yoshinori
, p. 610 - 611 (2014/05/20)
The total synthesis of cyclogalgravin and its dicarboxyl analog was achieved by using the SmI2-promoted Reformatsky type reaction and Sc(OTf)3-mediated diastereoselective ring expansion as key steps.
Collective synthesis of several 2,7′-cyclolignans and their correlation by chemical transformations
Peng, Yu,Luo, Zhen-Biao,Zhang, Jian-Jian,Luo, Long,Wang, Ya-Wen
, p. 7574 - 7586 (2013/11/06)
Collective synthesis of anti-malarial 2,7′-cyclolignans has been stereoselectively achieved employing (±)-cyclogalgravin (2) as a linchpin through a series of functional group conversions, including redox reactions. Interestingly, 2 can be correlated with
Synthesis of magnoshinin and cyclogalgravin: Modified stobbe condensation reaction
Yvon,Datta,Le,Charlton
, p. 1556 - 1560 (2007/10/03)
The development of new methods for lignan synthesis is reported. A recently reported method for the preparation of 1-aryl-1,2-dihydronaphthalenes is exploited to prepare magnoshinin, a naturally occurring lignan, and cyclogalgravin (3,4-dehydrogalbulin), a derivative of a natural lignan.
Structure of Malabaricanol - A Lignan from the Aril of Myristica malabarica Lam.
Purushothaman, K. K.,Sarada, A.,Connolly, J. D.
, p. 46 - 48 (2007/10/02)
Malabaricanol, a lignan isolated from Myristica malabarica has been assigned the structure as β,β'-dimethyl-α,α'-bis(4-hydroxy-3-methoxyphenyl)tetrahydrofuran by spectroscopic and chemical methods.
