135040-83-4Relevant articles and documents
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 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
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.