156769-17-4Relevant articles and documents
A LIGNAN FROM SCHIZANDRA CHINENSIS
Ikeya, Yukinobu,Taguchi, Heihachiro,Mitsuhashi, Hiroshi,Takeda, Shigefumi,Kase, Yoshio,Aburada, Masaki
, p. 569 - 574 (1988)
A new dibenzocyclooctadiene lignan, isoschizandrin was isolated from the fruits of Schizandra chinensis.The structure was elucidated on the basis of the spectral analysis and chemical correlation with schizandrin and (+)-deoxyschizandrin.In experiments using rats, schizandrin and its derivatives, including isoschizandrin, showed inhibitory effects on stress-induced gastric ulceration (p.o).Key Word Index-Schizandra chinensis; Schizandraceae; dibenzocyclooctadiene; lignan; isoschizandrin; anti-ulcer effect.
Ruthenium dioxide in fluoro acid medium V. Application to the non phenolic oxidative coupling of diarylbutanes. Conformational studies of cis and trans deoxyschizandrins
Dhal,Landais,Lebrun,Lenain,Robin
, p. 1153 - 1164 (2007/10/02)
Ruthenium (IV) dioxide dihydrate in fluoro acidic medium was found to be a very efficient agent for the non phenolic oxidative coupling of diarylbutanes. We observed along with the expected aryl-aryl coupling, an unusual aryl-benzyl coupling, leading to a known class of lignans, the aryltetralins. Conformational studies of resultant cis and trans deoxyschizandrins were performed using high resolution NMR and molecular models.
Intramolecular Oxidative Coupling of Aromatic Compounds. VII. A Convenient Synthesis of (+/-)-Deoxyschizandrin
Carroll, Anthony R.,Read, Roger W.,Taylor, Walter C.
, p. 1579 - 1590 (2007/10/02)
A convenient synthesis of (+/-)-deoxyschizandrin was achieved through the key step of reductive coupling of the bisacetonylbiphenyl (3).The latter compound was synthesized by oxidative cleavage of the bis olefin (5) formed by Claisen rearrangement of the bismethallyl ether of 2,2',4,4'-tetramethoxybiphenyl-3,3'-diol.The synthesis of 2,2',4,4'-tetramethoxy-6,6'-di(prop-1-enyl)biphenyl-3,3'-diol (2) is also described.The diphenolic oxidation of (2) did not lead to products with β,β' carbons linked.
SYNTHESIS OF DIARYLBUTANES FROM CORDIGERINES AND REINVESTIGATION OF THEIR OXIDATIVE COUPLINGS IN DEOXYSCHIZANDRINS. - AN UNUSUAL FORMATION OF PHENYLTETRALIN LIGNANS -
Landais, Y.,Lebrun, A.,Lenain, V.,Robin, J.-P.
, p. 5161 - 5164 (2007/10/02)
Dibenzylbutanolide lignans including cordigerines were synthetized and transformed in the corresponding diarylbutane lignans which were submitted to non-phenolic oxidative coupling conditions by using RuO2 or Tl2O3 in trifluoroacetic medium to give deoxyschizandrins.A concurently aryl-benzyl coupling leads to the formation of the corresponding phenyltetralin of which the structure was confirmed by total synthesis.
RUTHENIUM(IV) TETRAKIS(TRIFLUOROACETATE), A NEW OXIDIZING AGENT. II. A NEW ACCESS TO SCHIZANDRINS SKELETON USING BIARYL OXIDATIVE COUPLING OF CIS-SUBSTITUTED BUTANOLIDES
Landais, Y.,Lebrun, A.,Robin, J. P.
, p. 5377 - 5380 (2007/10/02)
The use of the title reagent -RUFTA- was applied to the first stereospecific synthesis of bridged biaryl lactones from the corresponding cis-2,3-dibenzyl- and 3-benzyl-2-benzyliden- butanolides, respectively.A short reduction sequence afforded deoxyschiza
