- Biomimetic Synthesis of Illicium Oligomeric Neolignans
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Six products have been isolated from the oxidative coupling of 4-allylphenol in the presence of FeIII; the distribution of products suggests that oligomeric neolignans associated with the family Illicium may also be non-enzymic products of oxidative coupling.
- Sy, Lai-King,Brown, Geoffrey D.
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- Nickel-catalyzed reductive deoxygenation of diverse C-O bond-bearing functional groups
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We report a catalytic method for the direct deoxygenation of various C-O bond-containing functional groups. Using a Ni(II) pre-catalyst and silane reducing agent, alcohols, epoxides, and ethers are reduced to the corresponding alkane. Unsaturated species including aldehydes and ketones are also deoxygenated via initial formation of an intermediate silylated alcohol. The reaction is chemoselective for C(sp3)-O bonds, leaving amines, anilines, aryl ethers, alkenes, and nitrogen-containing heterocycles untouched. Applications toward catalytic deuteration, benzyl ether deprotection, and the valorization of biomass-derived feedstocks demonstrate some of the practical aspects of this methodology.
- Cook, Adam,MacLean, Haydn,St. Onge, Piers,Newman, Stephen G.
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p. 13337 - 13347
(2021/11/20)
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- Synthesis method of magnolol
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The invention relates to a synthesis method of magnolol. The synthesis method comprises the following steps: (1) performing reaction on 1,1'-biphenyl-2,2'-diphenol serving as a raw material and allylhalide under the existence of alkali to prepare 2,2'-diallyl-1,1'-biphenyl; (2) dissolving the 2,2'-diallyl-1,1'-biphenyl into a solvent and performing rearrangement reaction under the existence of columbium pentachloride to obtain the magnolol. Compared with the conventional reaction system, the synthesis method has the characteristics of simple route, simplicity and convenience in operation, mild condition and the like.
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Paragraph 0020; 0022
(2019/01/16)
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- SYNTHESIS OF MAGNOLOL AND ITS ANALOGUE COMPOUNDS
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PROBLEM TO BE SOLVED: To provide a method for producing a magnolol, or a derivative or analogue thereof, which is applied to compositions for treating bacteria and/or inflammation related oral diseases. SOLUTION: A method for producing a magnolol in the figure or a derivative of the magnolol comprises brominating and converting 2,2'-bisphenol to 5,5'-dibromo-2,2'-bisphenol, protecting hydroxyl groups by reaction with methoxymethyl chloride; further reacting it with magnesium, an allyl bromide or a substituted allyl bromide; and then deprotecting it. (R is H, alkyl, or substituted or unsubstituted phenyl.) COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0071; 0072; 0073
(2016/10/08)
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- PROCESSES FOR MAKING MAGNOLOL AND DERIVATIVES THEREOF
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Described herein are high yield methods for making magnolol (5,5′-diallyl-biphenyl-2,2′-diol) and tetrahydro-magnolol (5,5′-dipropyl-biphenyl-2,2′-diol).
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Paragraph 0022-0024
(2014/12/09)
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- PROCESSES FOR MAKING MAGNOLOL AND DERIVATIVES THEREOF
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Described herein are high yield methods for making magnolol (5,5'-diallyl-biphenyl-2,2'-diol) and tetrahydromagnolol (5,5'-dipropyl-biphenyl-2,2'-diol).
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- SYNTHESIS OF MAGNOLOL AND ITS ANALOGUE COMPOUNDS
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A method is described for producing magnolol, or a derivative or analogue thereof. The method includes obtaining MOM ether of 5,5'-diallylbiphenyl-2,2'-diol or a derivative or analogue thereof and subsequently converting the MOM ether of 5,5'-diallylbiphenyl-2,2'-diol into magnolol or a derivative or analogue thereof.
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Page/Page column 15
(2011/09/30)
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- Cytotoxic neolignans: An SAR study
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The cytotoxic effects of different neolignans with the structure 1 were studied. The neolignans, magnolol 1 and honokiol 2 have been reported to inhibit the growth of several tumor cell lines in vitro and in vivo. The chemical structure of magnolol and honokiol consists of biphenyl skeleton with phenolic and allylic functionalities. Analogs of 1 and 2 containing different substitution have been studies for their effect on the growth of Hep-G2 and their structure-activity relationships were reported in this work.
- Kong, Zwe-Ling,Tzeng, Shin-Cheng,Liu, Yeuk-Chuen
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p. 163 - 166
(2007/10/03)
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- Enantioselective syntheses of (S)- and (R)-8,9 dihydroxydihydromagnolol
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8,9-Dihydroxydihydromagnolol 5 was synthesized in four steps in which the synthesis of magnolol 4 was improved and the absolute configuration of 5 was confirmed as (R).
- Gu, Wenxin,She, Xuegong,Pan, Xinfu,Yang, Teng-Kuei
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p. 1377 - 1380
(2007/10/03)
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- Synthesis of (-)-Monoterpenylmagnolol and Magnolol
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(-)-Monoterpenylmagnolol (3) was synthesized in eight steps from (+)-3,9-dibromocamphor (4) and the bis(methoxymethyl) ether (22) of 3-(4-hydroxyphenyl)-1-propanol.Fragmentation of an endo-3-aryl-9-bromocamphor (27) provided the correct absolute stereochemistry.In this total synthesis, dissolving metal conditions were developed to reduce enol phosphate and isopropenyl functions without concomitant reduction of an attached phenol.Palladium(0)-catalyzed cross-coupling of an arylzinc chloride with 4-allyl-2-iodophenyl methoxymethyl ether (34) provided the desired tricyclic 1,2,3,5-tetrasubstituted biaryl 41 in fair yield without optimization and with little isomerization of the allyl group.Magnolol (1) was also synthesized by aryl coupling of 34 and the methoxymethyl ether of 4-allyl-2-lithiophenol via the zinc chloride method as above, as well as from 5,5'-dibromo-2,2'-dimethoxybiphenyl (37) by allylation with allyltributylstannane followed by ether cleavage.
- Agharahimi, Mohamad R.,LeBel, Norman A.
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p. 1856 - 1863
(2007/10/02)
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- NEUROTROPHIC SESQUITERPENE-NEOLIGNANS FROM MAGNOLIA OBOVATA: STRUCTURE AND NEUROTROPHIC ACTIVITY
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Novel sesquiterpene-neolignans, eudesobovatols A (1) and B (2), eudesmagnolol (3), eudeshonokiols A (4) and B (5), clovanemagnolol (6), and caryolanemagnolol (7), have been isolated from the bark of Magnolia obovata.Their structures were elucidated to be sesquiterpenes (eudesmol, 4,4,8-trimethyltricyclo2,5>dodecane-1,9-diol, and clovanediol) combined through ether bond with neolignans such as obovatol, honokiol, and magnolol on the basis of spectral data, degradation, and/or synthesis.Compounds 1, 6, and 7 were found to exhibit interesting neurotrophic activity on a neuronal cell culture system derived from fetal rat hemisphere.
- Fukuyama, Yoshiyasu,Otoshi, Yukio,Miyoshi, Kumi,Nakamura, Kazuhiko,Kodama, Mitsuaki,et al.
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p. 377 - 392
(2007/10/02)
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- Structures of Eudesmagnolol and Eudeshonokiol, Novel Sesquiterpene-Neolignans Isolated from Magnolia obovata
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Eudesmagnolol and eudeshonokiol, isolated from the bark of Magnolia obovata, have been assigned to unprecedented structures linked via an ether bond between sesquiterpene, eudesmol, and neolignans, magnolol and honokiol, respectively.
- Fukuyama, Yoshiyasu,Otoshi, Yukio,Nakamura, Kazuhiko,Kodama, Mitsuaki,Sugawara, Michiharu,Nagaswa, Masakazu
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p. 295 - 296
(2007/10/02)
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- Synthesis of Biphenyls by Acid-Catalyzed Condensation of 1-Oxaspirodeca-6,9-diene-2,8-dinoe with Phenols or Phenol-ethers
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Acid catalyzed condensation reaction reactions of 1-oxaspirodeca-6,9-diene-2,8-dione (1) (quinolactone) with phenols and phenol-ethers 2a-i to yield biphenyls 3a-i and 4a-f were found to proceed by an elimination-addition mechanism.Keywords-- condensation; acid catalysis; biphenyl; quinol-lactone; phenol; phenol-ether; elimination-addition mechanism
- Takeya, Tetsuya,Okubo, Toruo,Tobinaga, Seisho
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p. 1762 - 1769
(2007/10/02)
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