62624-76-4Relevant academic research and scientific papers
Synthesis and applications of diphosphine ligands derived from the lignan hydroxymatairesinol
Brusentsev, Yury,Eklund, Patrik
, p. 260 - 263 (2015/03/14)
Highly efficient methods for synthetic modifications of the natural lignan hydroxymatairesinol into chiral diphosphines similar to DIOP were developed. Catalytic activity and induction of enantioselectivity for the prepared phosphines were evaluated in rh
Oxidative cyclisation of 3,4-dibenzyltetrahydrofurans using ruthenium tetra(trifluoroacetate)
Ward, Robert S,Hughes, David D
, p. 2057 - 2064 (2007/10/03)
A series of trans-3,4-dibenzyltetrahydrofurans has been synthesised and subjected to oxidative cyclisation using ruthenium tetra(trifluoroacetate), affording dibenzocyclooctadiene lignans belonging to the isostegane series, in high yields. Since no evidence was found for the formation of the corresponding stegane isomers it is assumed that the reactions proceed with complete diastereoselectivity.
Enantiocontrolled Synthesis of Burseran, Brassilignan, Dehydroxycubebin, and Other Tetrahydrofuran Lignans in Both Enantiomeric Forms. Application of Intermolecular Nitrile Oxide Cycloadditions and Lipase Mediated Kinetic Resolutions
Gaboury, Janet A.,Sibi, Mukund P.
, p. 2173 - 2180 (2007/10/02)
Several natural and unnatural tetrahydrofuran lignans have been synthesized by a convergent approach.Our methodology utilizes a nitrile oxide cycloaddition to dihydrofuran 8 and an enzymatic resolution of alcohols 11 by lipase PS.The lipase-mediated kinetic resolution of alcohols 11 furnished both enantiomers of the lignan precursors 12 and 14 in high optical purity (>99percent ee).This is followed by a SN2 displacement of tosylates 15 and 18 by α-lithiobenzyl phenyl sulfides.In this manner, both enantiomers of 3,4-dibenzyltetrahydrofuran (17a, 20a), 3,4-bis(3-methoxybenzyl)tetrahydrofuran (17b, 20b), brassilignan (17c, 20c), dehydroxy cubebin (17d, 20d), and burseran (17e, 20e) were synthesized in overall yields of 6-16percent.
Synthetic butanolide and tetrahydrofuran lignans with platelet activating factor antagonist activity
Coran, SA,Bambagiotti-Alberti, M,Melani, F,Giannellini, V,Vincieri, FF,et al.
, p. 643 - 650 (2007/10/02)
Several butanolide and tetrahydrofuran lignans were synthesized to be comparatively tested as platelet activating factor (PAF) antagonists.In particular, the influence of the tetrahydrofuranes ether oxygene as compared with the γ-lactone system of butanol
Oxidative aryl-aryl, aryl-benzyl coupling of lignans-reactions of phyllanthin and haloderivatives with TTFA, DDQ, Li/THF)))): Synthesis of dibenzocyclooctadiene system and phyltetralin
Satyanarayana,Venkateswarlu,Viswanatham
, p. 8277 - 8284 (2007/10/02)
Treatment of phyllanthin (1) with TTFA in TFA gives dibenzocyclooctadiene (2) and phyltetralin (3). Treatment of (1) with DDQ in TFA also affords (2) while with DDQ in acetic acid gives 1-phenylnaphthalenic lignan (4). Synthesis of halophyllanthins (5,6,7) and its Ullmann reaction in ultrasonic condition affords reductive dehalogenated product (1) instead of (2). Treatment of (1) with POCl3 in TCA gives (+) 3,4-diveratryltetrahydrofuran (8) and its conversion to (9) also reported. Treatment of (5) with TTFA/TFA gives (9).
LIGNANES.10. PREPARATION DES (R)-(+) ET (S)-(-)-β-PIPERONYL ET β-VERATRYL-γ-BUTYROLACTONES ET LEUR UTILISATION DANS LA SYNTHESE TOTALE DE LIGNANES OPTIQUEMENT ACTIFS
Brown, Eric,Daugan, Alain
, p. 141 - 154 (2007/10/02)
A simple and efficient route leading to optically active β-benzyl-γ-butyrolactones is described.Thus, the methyl (R,S)-α-benzylhemisuccinate resulting from a Stobbe condensation with an appropriate aromatic aldehyde, followed by catalytic hydrogenation of the intermediate α-benzylidene hemisuccinic ester, was resolved by means of a chiral base (ephedrine or α-methyl benzylamine).Reduction of each enantiomer, using calcium borohydride, then led to the corresponding optically active β-benzyl-γ-butyrolactone.In this way, the following two lactones were obtained in both (R)-(+) and (S)-(-) enantiomeric forms, β-piperonyl- and β-veratryl-γ-butyrolactones 1 and 2 respectively.These lactones were used as key-intermediates for the syntheses of 17 optically active lignans and lignoids, such as (-)-dimethylmatairesinol (-)-23, (-)-kusunokinin (-)-26 and (+)-dimethylisolariciresinol (+)-35.
Oxidative Coupling of Lignans. IV. Monophenolic Oxidative Coupling
Burden, Jonathan K.,Cambie, Richard C.,Craw, Peter A.,Rutledge, Peter S.,Woodgate, Paul D.
, p. 919 - 933 (2007/10/02)
Oxidative coupling of the monophenolic monoester (6) gives an aryltetralin (12) which is a potential intermediate for the synthesis of clinically active monophenolic lignan lactones.In contrast, oxidative couplings of the monophenols (32) and (35), derived from matairesinol (29), give mixtures of diastereoisomeric cyclooctadiene lignans while 4'-demethyldeoxypodorhizon (26) does not cyclize.These results show that the degree of aromatic substitution in monophenolic diarylbutanes plays an important role in determining the outcome of oxidative coupling.An alternative synthesis of the lactone (57) from piperonal has been investigated.
Oxidative Coupling of Lignans. II. Non-Phenolic Coupling of Diarylbutane Lignans Related to Matairesinol Dimethyl Ether
Buckleton, John S.,Cambie, Richard C.,Clark, George R.,Craw, Peter A.,Rickard, Clifton E. F.,et al.
, p. 305 - 324 (2007/10/02)
The non-phenolic oxidative coupling of some diarylbutane lignans related to matairesinol dimethyl ether (1) has been investigated.Coupling with a thallium(III) oxidant, prepared in situ from thallium(III) oxide and trifluoroacetic acid, converts these lig
