81410-45-9Relevant articles and documents
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
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.
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