{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,18]],"date-time":"2026-10-18T02:45:16Z","timestamp":1792291516503,"version":"4.4.0"},"reference-count":54,"publisher":"Wiley","issue":"15","license":[{"start":{"date-parts":[[2026,8,8]],"date-time":"2026-08-08T00:00:00Z","timestamp":1786147200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,8,8]],"date-time":"2026-08-08T00:00:00Z","timestamp":1786147200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemSusChem"],"published-print":{"date-parts":[[2026,8,14]]},"abstract":"<jats:p>\n                    We report a modular and scalable synthetic strategy for constructing a diverse library of oligomeric lignin model compounds (LMCs). Using bromoketoester building blocks, iterative \u03b2\u2010\n                    <jats:italic>O\u2010<\/jats:italic>\n                    4 aryl ether couplings under mild conditions enabled the efficient assembly of dimers, trimers, and tetramers. The developed approach is compatible with H, G, and S lignin units and can be extended to cinnamyl alcohols and \u03b2\u20105 linkages, mimicking the structural diversity of native lignin. Linear and convergent routes were demonstrated, and total reductions afforded final LMCs representative of lignins from various botanical sources. Our platform and advanced LMC library will allow studying lignin chemistry in unprecedented detail, bridging the gap between currently available dimers and actual polymeric lignin.\n                  <\/jats:p>","DOI":"10.1002\/cssc.70939","type":"journal-article","created":{"date-parts":[[2026,8,8]],"date-time":"2026-08-08T17:31:49Z","timestamp":1786210309000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Modular Synthesis of a Lignin Oligomer Library"],"prefix":"10.1002","volume":"19","author":[{"given":"Eman","family":"Abdelraheem","sequence":"first","affiliation":[{"name":"Laboratory of Organic Chemistry Wageningen University  Wageningen The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6944-887X","authenticated-orcid":false,"given":"Tom A.","family":"Ewing","sequence":"additional","affiliation":[{"name":"Wageningen Food &amp; Biobased Research  Wageningen The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1544-1744","authenticated-orcid":false,"given":"Gijs","family":"van Erven","sequence":"additional","affiliation":[{"name":"Wageningen Food &amp; Biobased Research  Wageningen The Netherlands"},{"name":"Laboratory of Food Chemistry Wageningen University  Wageningen The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6420-211X","authenticated-orcid":false,"given":"Fedor M.","family":"Miloserdov","sequence":"additional","affiliation":[{"name":"Laboratory of Organic Chemistry Wageningen University  Wageningen The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,8,8]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0EE02870C"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201510351"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biotechadv.2023.108230"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.copbio.2019.02.019"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.202000989"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b04144"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41570\u2010020\u20100187\u2010y"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586\u2010024\u201007446\u20105"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.202402334"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0OB00800A"},{"key":"e_1_2_8_12_1","unstructured":"To our knowledge only three lignin model compounds are commercially available all of which are \u03b2\u2010O\u20104 dimers: guaiacylglycerol\u2010\u03b2\u2010guaiacyl ether (G\u2010G) veratrylglycerol\u2010\u03b2\u2010guaiacyl ether (V\u2010G) and 1\u2010(4\u2010Hydroxy\u20103 5\u2010dimethoxyphenyl)\u20102\u2010(2\u2010methoxyphenoxy)propane\u20101 3\u2010diol (S\u2010G)."},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/A805027I"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo035052w"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/B805460F"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3GC41110A"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.3389\/fchem.2019.00842"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557\u2010021\u201000783\u20102"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.biomac.5c02761"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.trechm.2019.05.008"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202401911"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr900354u"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10086\u2010005\u20100756\u20101"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytol.2015.07.002"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.porgcoat.2022.107210"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1515\/znb\u20102016\u20100201"},{"key":"e_1_2_8_27_1","unstructured":"Methyl ester derivative of 1b was found to be a sticky oil that was difficult to handle and weigh precisely thus we synthesized the ethyl ester analogue which was a crystalline solid."},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol0358206"},{"key":"e_1_2_8_29_1","unstructured":"Performing bromination\/oxidation with DMP in two separate steps resulted in comparable yields as one\u2010pot protocols. The latter avoids additional workup and purification."},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00228a015"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.3891\/acta.chem.scand.43\u20100248"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1080\/00397919908086606"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.03.015"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(03)00736\u20106"},{"key":"e_1_2_8_35_1","unstructured":"Deposition Numbers 2524412 (for3a) 2524413 (for3i) 2524414 (for6) and 2524415 (forLMC5) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service."},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02969265"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12039\u2010014\u20100599\u20107"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.06.077"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.3184\/174751917x14931195075599"},{"key":"e_1_2_8_40_1","unstructured":"There is considerable overlap between different subunit\u2010diastereomer combinations (LMC1vsLMC6vsLMC4vsLMC9) so in more advanced oligomers and especially actual lignin care should be taken with annotations. Higher field magnets combined with a cryoprobe improve resolution and thus aid in resolving the various motifs."},{"key":"e_1_2_8_41_1","author":"Ralph S. 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