22614-13-7Relevant academic research and scientific papers
TRIP-Catalyzed Asymmetric Synthesis of (+)-Yatein, (-)-α-Conidendrin, (+)-Isostegane, and (+)-Neoisostegane
Hartmann, Peter,Lazzarotto, Mattia,Steiner, Lorenz,Cigan, Emmanuel,Poschenrieder, Silvan,Sagmeister, Peter,Fuchs, Michael
, p. 5831 - 5837 (2019)
The asymmetric allylation under the assistance of catalytic amounts of 3,3′-bis(2,4,6-triisopropylphenyl)-1,1′-binaphthyl-2,2′-diyl hydrogen phosphate (TRIP) allows the concise construction of the lignan scaffold from simple aldehydes and allylic bromides with full control of the two formed stereocenters. This young methodology has been employed to synthesize four naturally and pharmaceutically active lignans. Members of the dibenzylbutyrolactone, the tetraline, and the dibenzocyclooctadiene classes have been synthesized in 40-47% overall yield along four-step synthetic routes.
Syntheses of all eight stereoisomers of conidendrin
Nishiwaki, Hisashi,Shirakata, Hinako,Yamauchi, Satoshi
, p. 1 - 11 (2020/07/04)
All eight stereoisomers of conidendrin were synthesized from (1 R,2 S,3 S)-1-(4-benzyloxy-3-methoxyphenyl)-3-(4-benzyloxy-3-methoxybenzyl)-2- hydroxymethyl-1,4-butanediol ((+)-4) and its enantiomer with high optical purity. The configurations at 4-positio
Derivatives of the Lignan 7′-Hydroxymatairesinol with Antioxidant Properties and Enhanced Lipophilicity
Moraux, Thomas,Dumar?ay, Stéphane,Gérardin, Philippe,Gérardin-Charbonnier, Christine
supporting information, p. 1783 - 1790 (2017/06/28)
The lignan 7′-hydroxymatairesinol (1), extracted from the knotwoods of fir (Abies alba), spruce (Picea abies), and Douglas fir (Pseudotsuga menziesii), exhibited unexpected reactivity when esterification reactions were attempted on the hydroxy group at position C-7′. To circumvent the rapid intramolecular cyclization procedure, leading quantitatively to the lignan conidendrin (7), a simple strategy for 7′-esterification of 1 under mild conditions (three steps, up to 80% overall yield) was developed. Compared to hydroxymatairesinol (1) (log K′w = 1.49), the derivatives (2-5) had increased lipophilicity with log K′w > 3.1, as determined by a UHPLC method. Compounds 1-5 exhibited potent antioxidant properties in the same range as the standards ascorbic acid and α-tocopherol (IC50 = 20-25 μM) and higher than that of BHT using a DPPH radical-scavenging assay.
Gold particle size effect in biomass-derived lignan hydroxymatairesinol oxidation over Au/Al2O3 catalysts
López, Martín,Simakova, Olga A.,Murzina, Elena V.,Willf?r, Stefan M.,Prosvirin, Igor,Simakov, Andrey,Murzin, Dmitry Yu.
, p. 248 - 255 (2015/02/19)
The heterogeneously catalyzed aerobic selective oxidation of naturally occurring lignan hydroxymatairesinol (HMR) to another lignan oxomatairesinol (oxoMAT) was carried out at 70°C and atmospheric pressure over gold nanoparticles with different sizes supp
Synthesis and structural analysis of sterically hindered chiral 1,4-diol ligands derived from the lignan hydroxymatairesinol
Brusentsev, Yury,Sandberg, Thomas,Hotokka, Matti,Sj?holm, Rainer,Eklund, Patrik
supporting information, p. 1112 - 1115 (2013/04/10)
The readily available natural lignan hydroxymatairesinol was transformed into sterically hindered and optically pure diphenyl, di-2-naphthyl, and tetramethyl 1,4-diol derivatives via arylation/alkylation of the aryltetralinbutyrolactone lignan (-)-conidendrin. In addition, the diastereoselective formation of stable hemiketals from the highly substituted butyrolactone was studied in detail. The conformations of the molecules prepared were studied computationally at molecular mechanics (MM), Hartree-Fock (HF)/6-31G*, and (DFT/B3LYP/TZVP) levels including entropy contributions and by NMR-spectroscopy. The conformations adopted showed that these novel chiral 1,4-diols may be suitable as chiral ligands for the development of new chiral transition metal and organo catalysts.
Oxidative dehydrogenation of a biomass derived lignan - Hydroxymatairesinol over heterogeneous gold catalysts
Simakova, Olga A.,Murzina, Elena V.,Maeki-Arvela, Paeivi,Leino, Anne-Riikka,Campo, Betiana C.,Kordas, Krisztian,Willfoer, Stefan M.,Salmi, Tapio,Murzin, Dmitry Yu.
experimental part, p. 54 - 64 (2011/09/20)
Synthesis of the lignan oxomatairesinol via oxidative dehydrogenation of the naturally occurring lignan hydroxymatairesinol was studied over gold catalysts supported on C, TiO2, SiO2, Al2O 3, and MgO. In order to investigate the reaction performance over the gold catalyst, synthesis of lignan oxomatairesinol was carried out in different organic solvents/water mixtures under synthetic air and nitrogen atmosphere at 373 K, and using also isolated hydroxymatairesinol isomers as a starting material. The results were compared with those obtained over palladium catalysts. Synthesized supported gold catalysts as well as the corresponding supports were characterized by TEM, XRD, ICP-OES, CO2-TPD, FTIR (using pyridine as a probe molecule), and XPS. Gold catalysts were shown to display superior performance compared with palladium ones: the activity was 4 times higher, with selectivity toward oxomatairesinol being 100%, while 60-85% were obtained over palladium catalysts. In contrast to palladium, the activity of gold catalysts is high in aerobic conditions and water-propan-2-ol mixture. However, activity and selectivity of gold catalysts were shown to be dependent on the electronic state of the metal and, similar to palladium catalysts, on the support acidity.
Radical carboxyarylation approach to lignans. Total synthesis of (-)-arctigenin, (-)-matairesinol, and related natural products
Fischer, Joshua,Reynolds, Aaron J.,Sharp, Lisa A.,Sherburn, Michael S.
, p. 1345 - 1348 (2007/10/03)
Total syntheses of seven biologically important lignan natural products, including (-)-arctigenin, (-)-matairesinol, and (-)α-conidendrin, by way of a highly stereoselective domino radical sequence is presented. The reported stereochemistry of the natural product 7-hydroxyarctigenin is shown to be erroneous; a diastereoisomeric structure is assigned to the natural product.
Intermolecular C-H activation at benzylic positions: Synthesis of (+)-imperanene and (-)-α-conidendrin
Davies, Huw M. L.,Jin, Qihui
, p. 941 - 949 (2007/10/03)
An efficient C-H activation of primary benzylic positions by means of rhodium carbenoid induced C-H insertions is described. This key step was used in concise syntheses of (+)-imperanene and (-)-α-conidendrin.
ETUDES DE LIGNANES 7 - SYNTHESES TOTALES DES (+-)-α ET -β-CONIDENDRINES ET DES METHYL (+-)-α ET -β-CONIDENDRALS
Dhal, Robert,Nabi, Yahia,Brown, Eric
, p. 2005 - 2016 (2007/10/02)
Michael addition of the carbanion of the dithian 8 on butenolide, followed by alkylation with the benzylic bromide 11 and regeneration of the ketonic carbonyl group, gave the α,β-disubstituted lactone 13.Reduction of the ketonic carbonyl of the latter usi
