{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:37:18Z","timestamp":1786977438139,"version":"build-2736575974"},"reference-count":59,"publisher":"Wiley","issue":"27","license":[{"start":{"date-parts":[[2024,3,27]],"date-time":"2024-03-27T00:00:00Z","timestamp":1711497600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["Schu984 13\/1"],"award-info":[{"award-number":["Schu984 13\/1"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2024,5,14]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Springtails use unique compounds for their outermost epicuticular wax layer, often of terpenoid origin. We report here the structure and synthesis of socialane, the major cuticular constituent of the Collembola\n                    <jats:italic>Hypogastrura socialis<\/jats:italic>\n                    . Socialane is also the first regular nonaprenyl terpene with a cyclic head group. The saturated side chain has seven stereogenic centers, making the determination of the configuration difficult. We describe here the identification of socialane and a synthetic approach using the building blocks farnesol and phytol, enantioselective hydrogenation, and \u03b1\u2010alkylation of sulfones for the synthesis of various stereoisomers. NMR experiments showed the presence of an\n                    <jats:italic>anti<\/jats:italic>\n                    \u2010configuration of the methyl groups closest to the benzene ring and that the other methyl groups of the polyprenyl side\u2010chain are not uniformly configured. Furthermore, socialane is structurally different from [6+2]\u2010terpene viaticene of the closely related\n                    <jats:italic>H. viatica<\/jats:italic>\n                    , showing species specificity of the epicuticular lipids of this genus and hinting at a possible role of surface lipids in the communication of these gregarious arthropods.\n                  <\/jats:p>","DOI":"10.1002\/chem.202400272","type":"journal-article","created":{"date-parts":[[2024,3,6]],"date-time":"2024-03-06T05:04:47Z","timestamp":1709701487000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Socialane, a Nonaprenyl Terpene Hydrocarbon Surface Lipid from the Collembola\n                    <i>Hypogastrura socialis<\/i>"],"prefix":"10.1002","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0009-0003-3944-520X","authenticated-orcid":false,"given":"Anton","family":"M\u00f6llerke","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry Technische Universit\u00e4t Braunschweig  Hagenring 30 38106 Braunschweig Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1157-4179","authenticated-orcid":false,"given":"Diogo","family":"Montes Vidal","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry Technische Universit\u00e4t Braunschweig  Hagenring 30 38106 Braunschweig Germany"},{"name":"Department of Chemistry, ICEx Universidade Federal de Minas Gerais  Av. Antonio Carlos 6627 31270-901 Belo Horizonte Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6628-6767","authenticated-orcid":false,"given":"Hans","family":"Petter Leinaas","sequence":"additional","affiliation":[{"name":"Department of Bioscience University of Oslo  Postboks 1066, Blindern, 0316 Oslo Norway"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4810-324X","authenticated-orcid":false,"given":"Stefan","family":"Schulz","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry Technische Universit\u00e4t Braunschweig  Hagenring 30 38106 Braunschweig Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,3,27]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201900224"},{"key":"e_1_2_8_2_1","unstructured":"\u00a0"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-12-409547-2.14624-4"},{"key":"e_1_2_8_4_2","first-page":"87","volume-title":"Nat. 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