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With essential immunoregulatory roles, phosphatidylinositol mannosides are among the cell-envelope components critical to the pathogenesis and survival of <jats:italic>M. tuberculosis<\/jats:italic> inside its host. Here we report the first synthesis of the highly complex tetraacylated phosphatidylinositol hexamannoside (Ac<jats:sub>2<\/jats:sub>PIM<jats:sub>6<\/jats:sub>), having stearic and tuberculostearic acids as lipid components. Our effort makes use of stereoelectronic and steric effects to control the regioselective and stereoselective outcomes and minimize the synthetic steps, particularly in the key desymmetrization and functionalization of <jats:italic>myo<\/jats:italic>-inositol. A short synthesis of tuberculostearic acid in six steps from the Roche ester is also described. Mice exposed to the synthesized Ac<jats:sub>2<\/jats:sub>PIM<jats:sub>6<\/jats:sub> exhibit increased production of interleukin-4 and interferon-\u03b3, and the corresponding adjuvant effect is shown by the induction of ovalbumin- and tetanus toxoid-specific antibodies.<\/jats:p>","DOI":"10.1038\/ncomms8239","type":"journal-article","created":{"date-parts":[[2015,6,3]],"date-time":"2015-06-03T10:25:03Z","timestamp":1433327103000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":30,"title":["Total synthesis of tetraacylated phosphatidylinositol hexamannoside and evaluation of its immunomodulatory activity"],"prefix":"10.1038","volume":"6","author":[{"given":"Pratap S.","family":"Patil","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ting-Jen Rachel","family":"Cheng","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Medel Manuel L.","family":"Zulueta","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shih-Ting","family":"Yang","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Larry S.","family":"Lico","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shang-Cheng","family":"Hung","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"297","published-online":{"date-parts":[[2015,6,3]]},"reference":[{"key":"BFncomms8239_CR1","unstructured":"WHO. 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