117407-00-8Relevant academic research and scientific papers
New synthetic route to butanolide lignans by a ruthenium complex catalyzed hydrogenation of the corresponding Stobbe's fulgenic acids
Bambagiotti-Alberti, Massimo,Coran, Silvia A.,Vincieri, Franco F.,Mulinacci, Nadia,Pieraccini, Giuseppe M.L.
, p. 2185 - 2196 (1988)
A new two-step total synthesis of butanolide lignans (or dibenzylbutyrolactone lignans) is described, which affords the title compounds in good yield and with a very short work-up time. It involves a ruthenium carbonyl hydride complex-catalyzed hydrogenation of the corresponding dibenzylidene succinic acids (fulgenic acids). Since the catalytic hydrogenation (second step) is a total yielding process, the overall yield determining step is the preparation of the fulgenic acid intermediates by the Stobbe condensation (first step), which has consequently been revised to improve many details. This simple process moreover allows hexadeuterated butanolide lignans to be readily obtained for isotopic dilution mass spectral measurements. The syntheses of a selection of lignans, namely enterolactone, matairesinol, hinokinin, dimethylmatairesinol and cordigerine, are described to illustrate the whole procedure.
Simple synthesis of trans-α,β-dibenzyl-γ-butyrolactone lignans by diastereoselective reduction of α-benzylidene-β-benzyl-γ-butyralactones using NaBH4-NiCl2
Moritani,Fukushima,Miyagishima,Ohmizu,Iwasaki
, p. 2281 - 2286 (2007/10/03)
trans-α,β-Dibenzyl-γ-butyrolactone lignans were synthesized by stereoselective reduction of α-benzylidene-β-benzyl-γ-butyrolactones using NaBH4-NiCl2. The reduction is found to proceed via conjugate addition of a hydride to an α-benz
The Migration of Double Bond under the Neutral Conditions. The Transformation of α-Alkylidene Cyclic Carbonyl Compounds to α,β-Unsaturated Cyclic Carbonyl Compounds
Tanaka, Masahide,Mitsuhashi, Hiroshi,Maruno, Masao,Wakamatsu, Takeshi
, p. 1455 - 1458 (2007/10/02)
The transformation of α-alkylidene cyclic carbonyl compounds to α,β-unsaturated cyclic carbonyl compounds was achieved.In the presence of catalytic amount of triethylsilane, tris(triphenylphosphine)rhodium chloride was found to affect the migration of dou
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.
Process for the preparation of polycyclic compounds using ferric perchlorate and acid trifluoroacidic
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, (2008/06/13)
Polycyclic compounds (I) can be prepared in accordance with the following reaction formula: STR1 wherein R1 -R8 each represents a hydrogen atom, a hydroxyl group, an alkoxyl group or a substituted or unsubstituted benzyloxy group or
Polycyclic compounds, their preparation and their use as phosphodiesterases inhibitors
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, (2008/06/13)
Polycyclic compounds (I) can be prepared in accordance with the following reaction formula: wherein R1-R8 each represents a hydrogen atom, a hydroxyl group, an alkoxyl group or a substituted or unsubstituted benzyloxy group or neighb
STEREOSELECTIVE SYNTHESIS OF METHOXY SUBSTITUTED 2,3-DIBENZYL-γ-BUTYROLACTONES USING ORGANIC PHOSPHONATES AS INTERMEDIATES
Compagnone, Reinaldo S.,Suarez, Alirica
, p. 35 - 38 (2007/10/02)
A stereoselective, short and convergent synthesis of methoxy substituted 2,3-dibenzyl-γ-butyrolactones was developed using organic phosphonates as key intermediates.
Stereoselective synthesis of methoxy substituted 2,3-dibenzylbutyrolactones via organic phosphonates
Compagnone,Suarez
, p. 3041 - 3051 (2007/10/02)
A highly convergent, short and stereoselective synthesis of a series of methoxy substituted 2,3-dibenzylbutyrolactones was achieved using a Horner-Wadsworth-Emmons (HWE) reaction as the key step in overall yields above 32%.
Ruthenium dioxide in fluoro acid medium: I. A new agent in the biaryl oxidative coupling. Application to the synthesis of non phenolic bisbenzocyclooctadiene lignan lactones
Landais,Robin,Lebrun
, p. 3787 - 3804 (2007/10/02)
Ruthenium (IV) dioxide dihydrate in fluoro acid medium was found to be a very efficient agent for the oxidative coupling of non phenolic lignans and their derivatives, and this method was applied to the total synthesis of (+/-)-neoisostegane 2a and (+/-)-steganolide A 2b. This procedure was also used to obtain the first stereospecific synthesis of a cis-bisbenzocyclooctadiene lactone, the (+/-)-deoxyschizandrin 17, of which, was afforded by a short reduction sequence.
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.
