135040-83-4Relevant academic research and scientific papers
Revealing the fate of the phenylcoumaran linkage during lignin oxidation reactions
Lahive, Ciaran W.,Lancefield, Christopher S.,Codina, Anna,Kamer, Paul C. J.,Westwood, Nicholas J.
, p. 1976 - 1982 (2018)
The fate of most lignin linkages, other than the β-O-4, under selective oxidation conditions is largely unknown. In this work we use advanced β-5 lignin model compounds to identify the fate of phenylcoumaran units in a softwood lignin during oxidation with DDQ. By using model compounds combined with detailed characterisation of the oxidised lignin polymer using HSQC and HMBC NMR we show that phenylcoumarones are a major product, and therefore constitute a novel non-native β-5 linkage in oxidised lignins. Additionally, the reactivity of these units in lignin led us to further investigate their connectivity in lignin, showing that they are found as both phenolic and etherified units. The findings and approach developed here will help improve the efficiency of selective oxidative lignin depolymerisation processes, particularly those aimed at the upgrading of softwood lignin in which phenylcoumarans are a major linkage.
Synthesis of natural products possessing a benzo[b]furan skeleton
Luetjens, Henning,Scammells, Peter J.
, p. 6581 - 6584 (1998)
A related synthetic strategy has been used to prepare two natural products XH-14 and ailanthoidol) which possess a benzo[b]furan skeleton. The synthesis of XH-14 involved the use of a palladium-catalyzed cyclization with concomitant carbonylation via insertion of carbon monoxide to introduce regioselectively a formyl group in the 3-position.
Synthesis of Thio-lignan Analogues, Bioequivalent Salvinal without Unfavored Aldehyde
Saito, Yohei,Kobayashi, Yukiko,Yoshida, Nanami,Goto, Masuo,Nakagawa-Goto, Kyoko
, p. 7092 - 7106 (2021/05/29)
The oxygen in the benzofuran (BF) of three antiproliferative natural neolignans, salvinal (1), obovaten (2), and 2-[7-methoxy-2-(4-methoxyphenyl)-3-methylbenzofuran-5-yl]ethanol (3), was replaced with sulfur to form the new biological scaffold benzothioph
CAFFEIC ACID DERIVATIVES FOR ANTI-ANGIOGENESIS
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Paragraph 0045; 0081, (2016/12/22)
The present invention develops a series of methyl caffeate derivatives having biological activity in anti-angiogenesis. The present invention suggests that the compounds of the invention possess inhibiting angiogenesis through regulation of VEGF/VEGFR-2 a
Facile total synthesis of benzo[b]furan natural product XH-14
Bang, Hyun Bae,Han, Su Young,Choi, Da Hye,Yang, Deok Mo,Hwang, Jung Woon,Lee, Hyun Suck,Jun, Jong-Gab
experimental part, p. 506 - 515 (2009/06/28)
An efficient and practical total synthesis of benzo[b]furan natural product XH-14 is demonstrated in nine steps from vanillin. Introduction of iodide substituents in the reaction including optimization of the reaction sequences is essential for the successful synthesis of XH-14. Sonogashira coupling with iodobenzene, iodine-induced cyclization, Wittig reaction, and formylation are critical in the high-yield total synthesis of XH-14. Copyright Taylor & Francis Group, LLC.
A concise and efficient synthesis of salvinal from isoeugenol via a phenoxenium ion intermediate
Wang, Eng-Chi,Wein, Yung-Shung,Kuo, Yueh-Hsiung
, p. 9195 - 9197 (2007/10/03)
In this letter, we describe how salvinal can be efficiently synthesized from isoeugenol via a phenoxenium ion intermediate by four steps in 23% over all total yield.
A novel strategy for the synthesis of benzofuran skeleton neolignans: Application to ailanthoidol, XH-14, and obovaten
Kao, Chai-Lin,Chern, Ji-Wang
, p. 6772 - 6787 (2007/10/03)
A convenient and general approach to the synthesis of the benzofuran skeleton compounds ailanthoidol, XH-14, and obovaten was developed. Starting from vanillin, a series of reactions afforded 7 in 71% yield. Treatment of 7 with n-BuLi followed by addition of substituted benzaldehydes resulted in the formation of carbinols 11 and 31. The substituted benzophenones obtained from oxidation of 11 and 31 were treated with trimethylsilyldiazomethane lithium salt to give diphenylacetylenes 15 and 33, respectively. 15 and 33 were then cyclized in the presence of either mercury acetate in acetic acid or bromine in chloroform to give 3-chloromercurio- or 3-bromobenzofuran, respectively. The 3-chloromercurio intermediates could be reduced to proton or derivatized to ester or bromide, leading to the synthesis of ailanthoidol, XH-14, and obovaten, respectively. In addition, necleophilic substitution was used to introduce a formyl or methyl group into the 3-bromobenzofuran derivatives, providing an alternative pathway to XH-14 and obovaten. The final elongation and deprotection reaction furnished the desired ailanthoidol, XH-14, and obovaten in yields of 30, 15, and 11%, respectively.
Synthesis of 2-substituted 3-acylbenzo[b]furans via the palladium catalysed carbonylative cyclisation of ortho-hydroxytolans
Lütjens, Henning,Scammells, Peter J.
, p. 1079 - 1081 (2007/10/03)
A palladium-catalysed cyclisation with concomitant carbonylation via insertion of carbon monoxide was used to prepare several potential adenosine antagonists possessing a benzo[b]furan skeleton with a formyl group in the 3-position.
A new synthesis of the benzofuran adenosine antagonist XH-14
Hutchinson, Sally A.,Luetjens, Henning,Scammells, Peter J.
, p. 3081 - 3084 (2007/10/03)
5-(3-Hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzo[b]furan-3 -carbaldehyde (XH-14, 1) has been reported to be a potent A1 adenosine antagonist. We have developed an efficient synthesis of this compound that should prove valuable for further structure-activity studies. The synthesis incorporates optimised methodology for the selective protection of a hydroxyl group and the ortho-bromination of a phenol.
Regioselective Introduction of Carbon-3 Substituents to 5-Alkyl-7-methoxy-2-phenylbenzofurans: Synthesis of a Novel Adenosine A1 Receptor Ligand and Its Derivatives
Yang, Zhen,Liu, Han Biao,Lee, Chi Ming,Chang, Hson Mou,Wong, Henry N. C.
, p. 7248 - 7257 (2007/10/02)
By maintaining the balance between the electronic requirements, the stereochemical restrictions as well as the kinetic and thermodynamic factors, the unprecedented regioselective electrophilic aromatic substitution of formyl and nitro groups to carbon-3 o
