{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,25]],"date-time":"2026-06-25T09:51:55Z","timestamp":1782381115706,"version":"3.54.5"},"reference-count":16,"publisher":"Wiley","issue":"21","license":[{"start":{"date-parts":[[2016,4,13]],"date-time":"2016-04-13T00:00:00Z","timestamp":1460505600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"MINECO"},{"DOI":"10.13039\/501100008530","name":"FEDER","doi-asserted-by":"crossref","award":["CTQ2012-30930"],"award-info":[{"award-number":["CTQ2012-30930"]}],"id":[{"id":"10.13039\/501100008530","id-type":"DOI","asserted-by":"crossref"}]},{"DOI":"10.13039\/501100002809","name":"Generalitat de Catalunya","doi-asserted-by":"crossref","award":["2014 SGR 137"],"award-info":[{"award-number":["2014 SGR 137"]}],"id":[{"id":"10.13039\/501100002809","id-type":"DOI","asserted-by":"crossref"}]},{"name":"Institute for Research in Biomedicine Barcelona (IRB Barcelona)"},{"name":"Spanish Ministry of Education"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2016,5,17]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The terminal bromomethoxydiene (BMD) moiety of the polyhydroxylated chain present in phormidolides and oscillariolides has been synthesized for first time. Several strategies for the stereoselective synthesis of the 4\u2010bromo\u20103\u2010methoxybut\u20103\u2010en\u20102\u2010ones are described. Furthermore, a preliminary study to successfully introduce the BMD within the polyol chain and the fatty acid allowed us to corroborate the end structure of the polyol.<\/jats:p>","DOI":"10.1002\/chem.201600770","type":"journal-article","created":{"date-parts":[[2016,3,21]],"date-time":"2016-03-21T23:23:32Z","timestamp":1458602612000},"page":"7033-7035","source":"Crossref","is-referenced-by-count":10,"title":["Synthesis of (<i>E<\/i>)\u20104\u2010Bromo\u20103\u2010methoxybut\u20103\u2010en\u20102\u2010one, the Key Fragment in the Polyhydroxylated Chain Common to Oscillariolide and Phormidolides A\u2013C"],"prefix":"10.1002","volume":"22","author":[{"given":"Alejandro","family":"Gil","sequence":"first","affiliation":[{"name":"Institute for Research in Biomedicine Barcelona Science Park-University of Barcelona  Baldiri i Reixac 10 08028 Barcelona Spain"},{"name":"CIBER-BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine  08028 Barcelona Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Janire","family":"Lamariano\u2010Merketegi","sequence":"additional","affiliation":[{"name":"Institute for Research in Biomedicine Barcelona Science Park-University of Barcelona  Baldiri i Reixac 10 08028 Barcelona Spain"},{"name":"CIBER-BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine  08028 Barcelona Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Adriana","family":"Lorente","sequence":"additional","affiliation":[{"name":"Institute for Research in Biomedicine Barcelona Science Park-University of Barcelona  Baldiri i Reixac 10 08028 Barcelona Spain"},{"name":"CIBER-BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine  08028 Barcelona Spain"},{"name":"University of Zurich  Winterthurerstrasse 190 8057 Z\u00fcrich Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fernando","family":"Albericio","sequence":"additional","affiliation":[{"name":"CIBER-BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine  08028 Barcelona Spain"},{"name":"Department of Organic Chemistry University of Barcelona  08028 Barcelona Spain"},{"name":"School of Chemistry University of Kwa-Zulu-Natal  4001 Durban South Africa"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2025-9111","authenticated-orcid":false,"given":"Mercedes","family":"\u00c1lvarez","sequence":"additional","affiliation":[{"name":"Institute for Research in Biomedicine Barcelona Science Park-University of Barcelona  Baldiri i Reixac 10 08028 Barcelona Spain"},{"name":"CIBER-BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine  08028 Barcelona Spain"},{"name":"Laboratory of Organic Chemistry Faculty of Pharmacy  08028 Barcelona Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2016,4,13]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)79931-X"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo020240s"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201404341"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4NP00144C"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b03252"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201402987"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303192"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.199719970704"},{"key":"e_1_2_2_9_1","unstructured":"US-3646218A19720229 1972."},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00099a037"},{"key":"e_1_2_2_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00133a023"},{"key":"e_1_2_2_12_1","unstructured":"See the Supporting Information."},{"key":"e_1_2_2_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo991822l"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2015.11.050"},{"key":"e_1_2_2_15_1","unstructured":"The chemical shift of the vinylic proton in the two stereoisomers of1show an important difference due to the influence of bromide and methoxy groups. 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