biostudies-literatureHicks HBVertex PharmaceuticalsSyngenta InternationalGlaxoSmithKlineUniversity of OxfordBiotechnology and Biological Sciences Research CouncilMerck Sharp and Dohme9174-9178https://www.ebi.ac.uk/biostudies/studies/S-EPMC9791679biostudies-literatureUnknown24(50)The (<i>E</i>/<i>Z</i>)-ocellenynes are C₁₅ dibrominated <i>Laurencia</i> natural products whose structures have been subject to several reassignments on the basis of extensive NMR analysis, biosynthetic postulates, and DFT calculations. Herein, we report the synthesis of both (<i>E</i>)- and (<i>Z</i>)-ocellenyne, which, in combination with single crystal X-ray diffraction studies, allows their absolute configuration to be established and defines the configuration of the <i>syn</i>-12,13-dibromide as being (<i>S</i>, <i>S</i>) in keeping with their proposed biogenesis from the (6<i>S</i>, 7<i>S</i>)-laurediols.Organic lettersTotal Synthesis and Structure Confirmation of (<i>E</i>) and (<i>Z</i>)-Ocellenyne.PMC9791679BB/P504890/1Brown DSSousa BAChristensen KEHicks HBBurton JWSam Chan HSfalseTotal Synthesis and Structure Confirmation of (<i>E</i>) and (<i>Z</i>)-Ocellenyne.The (<i>E</i>/<i>Z</i>)-ocellenynes are C₁₅ dibrominated <i>Laurencia</i> natural products whose structures have been subject to several reassignments on the basis of extensive NMR analysis, biosynthetic postulates, and DFT calculations. Herein, we report the synthesis of both (<i>E</i>)- and (<i>Z</i>)-ocellenyne, which, in combination with single crystal X-ray diffraction studies, allows their absolute configuration to be established and defines the configuration of the <i>syn</i>-12,13-dibromide as being (<i>S</i>, <i>S</i>) in keeping with their proposed biogenesis from the (6<i>S</i>, 7<i>S</i>)-laurediols.2022-01-01T00:00:00Z2022 Dec2025-04-05T08:46:59.489Z2024-11-08T13:28:01.383ZS-EPMC97916793650849210.1021/acs.orglett.2c03524