81410-45-9Relevant academic research and scientific papers
Synthesis and bioactivity of erythro-nordihydroguaiaretic acid, threo-(-)-saururenin and their analogues
Xia, Yamu,Zhang, Yuanyuan,Wang, Wei,Ding, Yining,He, Rui
experimental part, p. 1325 - 1335 (2011/09/12)
Full details of the total syntheses of erythro-nordihydroguaiaretic acid, threo-(-)-saururenin and their analogues are presented. The syntheses were based on a unified synthetic strategy involving the Stobbe reaction, alkylation to construct the skeleton
Oxidative Homocoupling of Chiral 3-Arylpropanoic Acid Derivatives. Application to Asymmetric Synthesis of Lignans
Kise, Naoki,Ueda, Takako,Kumada, Kimikage,Terao, Yuichi,Ueda, Nasuo
, p. 464 - 468 (2007/10/03)
The oxidative homocouplings of lithium enolates of (4S)-3-(3-arylpropanoyl)-4-isopropyl-2-oxazolidinones and (4R,5S)-1-(3-arylpropanoyl)-3,4-dimethyl-5-phenyl-2-imidazolidinones gave the corresponding R,R-dimers stereoselectively with TiCl4, Ph
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.
General Conjugate-Addition Method for the Synthesis of Enantiomerically Pure Lignans. Total Synthesis of (-)- and (+)-Burseran, (-)-Dehydroxycubebin, (-)-Trichostin, (-)-Cubebin, (-)-5''-Methoxyhinokinin, and (-)-Hinokinin
Rehnberg, Nicola,Magnusson, Goeran
, p. 4340 - 4349 (2007/10/02)
Conjugate addition of benzylic diphenyldithioacetal anions to enantiomerically pure (-)-(2R)-and (+)-(2S)-(benzyloxy)-2,5-dihydro-4-furan (2 r and 2 s) gave complete lignan skeletons of the dibenzylbutane class.Desulfurization followed by hydrogenolysis and, when appropriate, oxidation gave the title enantiomerically pure > 99 percent ee) lignans 45 - 50 in 24 - 35 percent overall yields from 2 r and 2 s.
LIGNANDS FROM NECTANDRA TURBACENSIS
Carvalho, Mario G. De,Yoshida, Massayoshi,Gottlieb, Otto R.,Gottlieb Hugo E.
, p. 265 - 268 (2007/10/02)
Bark and wood of Nectanandra turbacensis (Lauraceae) contain, besides the known furofuran lignands (+)-sesamin, (+)-demethoxyexcelsin and (+)-piperitol, the novel (1R,5R,2S,6S)-2-(3'-methoxy-4',5'-methylenedioxyphenyl)-6-(4"-hydroxy-3"-methoxyphenyl)-3,7-dioxabicyclooctane and (1R,2S,5R)-2-(3'-methoxy-4',5'-methylenedioxyphenyl)-3,7-dioxa-6-oxobicyclooctane. Key Word Index--Nectandra turbacensis; Lauraceae; furofuran lignands; 2-aryl-3,7-dioxa-6-oxobicyclooctane
NEM LIGNANS FROM THE HEARTWOOD OF CLEISTANTHUS COLLINUS
Anjaneyulu, A. S. R.,Ramaiah, P. Atchuta,Row, L. Ramachandra,Venkateswarlu, R.,Pelter, A.,Ward, R. S.
, p. 3641 - 3652 (2007/10/02)
The isolation and characterisation of five new compounds and nine known compounds from the heartwood of Cleistanthus collinus are reported.The new compounds are wodeshiol 16, 3,4-dihydrotaiwanin C 20, and three new glycosides 24, 25 and 26 of diphyllin and taiwanin E.The 1H and 13C NMR spectra of these compounds are also reported.
