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The structure was determined by a combination of NMR spectroscopy, HRMS, X\u2010ray diffraction studies and Mosher's analysis of the base hydrolysis product. Its carbon skeleton closely resembles that of clavosolides A\u2013D isolated from the sponge <jats:italic>Myriastra clavosa<\/jats:italic>, for which no bioactivity is known. We performed the first total synthesis of cocosolide (<jats:bold>1<\/jats:bold>) along with its [<jats:italic>\u03b1,\u03b1<\/jats:italic>]\u2010anomer (<jats:bold>26<\/jats:bold>) and macrocyclic core (<jats:bold>28<\/jats:bold>), thus leading to the confirmation of the structure of natural <jats:bold>1<\/jats:bold>. The convergent synthesis featured Wadsworth\u2013Emmons cyclopropanation, Sakurai annulation, Yamaguchi macrocyclization\/dimerization reaction, \u03b1\u2010selective glycosidation and \u03b2\u2010selective glycosidation. Compounds <jats:bold>1<\/jats:bold> and <jats:bold>26<\/jats:bold> potently inhibited IL\u20102 production in both T\u2010cell receptor dependent and independent manners. Full activity requires the presence of the sugar moiety as well as the intact dimeric structure. Cocosolide also suppressed the proliferation of anti\u2010CD3\u2010stimulated T\u2010cells in a dose\u2010dependent manner.<\/jats:p>","DOI":"10.1002\/chem.201600674","type":"journal-article","created":{"date-parts":[[2016,5,3]],"date-time":"2016-05-03T08:28:25Z","timestamp":1462264105000},"page":"8158-8166","source":"Crossref","is-referenced-by-count":31,"title":["Discovery, Total Synthesis and Key Structural Elements for the Immunosuppressive Activity of Cocosolide, a Symmetrical Glycosylated Macrolide Dimer from Marine Cyanobacteria"],"prefix":"10.1002","volume":"22","author":[{"given":"Sarath P.","family":"Gunasekera","sequence":"first","affiliation":[{"name":"Smithsonian Marine Station  701 Seaway Drive Fort Pierce Florida 34949 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yang","family":"Li","sequence":"additional","affiliation":[{"name":"Laboratory of Chemical Genomics School of Chemical Biology and Biotechnology Shenzhen Graduate School of Peking University  Shenzhen 518055 P.R. 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