{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,2]],"date-time":"2026-06-02T05:08:26Z","timestamp":1780376906992,"version":"3.54.1"},"reference-count":40,"publisher":"Beilstein Institut","license":[{"start":{"date-parts":[[2021,3,11]],"date-time":"2021-03-11T00:00:00Z","timestamp":1615420800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2021,3,11]],"date-time":"2021-03-11T00:00:00Z","timestamp":1615420800000},"content-version":"am","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2021,3,11]],"date-time":"2021-03-11T00:00:00Z","timestamp":1615420800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Beilstein J. Org. Chem."],"accepted":{"date-parts":[[2021,2,26]]},"abstract":"<jats:p>\n                    The efficient synthesis of two new stereoisomeric 3-aminocyclooctanetriols and their new halocyclitol derivatives starting from\n                    <jats:italic>cis,cis<\/jats:italic>\n                    -1,3-cyclooctadiene are reported. Reduction of cyclooctene endoperoxide, obtained by photooxygenation of\n                    <jats:italic>cis,cis<\/jats:italic>\n                    -1,3-cyclooctadiene, with zinc yielded a cyclooctene diol followed by acetylation of the hydroxy group, which gave dioldiacetate by OsO\n                    <jats:sub>4<\/jats:sub>\n                    \/NMO oxidation. The cyclooctane dioldiacetate prepared was converted to the corresponding cyclic sulfate via the formation of a cyclic sulfite in the presence of catalytic RuO\n                    <jats:sub>4<\/jats:sub>\n                    . The reaction of this cyclic sulfate with a nucleophilic azide followed by the reduction of the azide group provided the target, 3-aminocyclooctanetriol. The second key compound, bromotriol, was prepared by epoxidation of the cyclooctenediol with\n                    <jats:italic>m<\/jats:italic>\n                    -chloroperbenzoic acid followed by hydrolysis with HBr(g) in methanol. Treatment of bromotriol with NaN\n                    <jats:sub>3<\/jats:sub>\n                    and the reduction of the azide group yielded the other desired 3-aminocyclooctanetriol. Hydrolysis of the epoxides with HCl(g) in methanol gave stereospecifically new chlorocyclooctanetriols.\n                  <\/jats:p>","DOI":"10.3762\/bjoc.17.59","type":"journal-article","created":{"date-parts":[[2021,3,11]],"date-time":"2021-03-11T07:36:35Z","timestamp":1615448195000},"page":"705-710","source":"Crossref","is-referenced-by-count":6,"title":["Stereoselective syntheses of 3-aminocyclooctanetriols and 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