Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols

  1. Emine SalamciORCID Logo and
  2. Yunus ZozikORCID Logo

Submitting author affiliation: Atatürk University, Erzurum, Turkey

Beilstein Arch. 2020, 2020142. https://doi.org/10.3762/bxiv.2020.142.v1

Published 14 Dec 2020

  • Preprint

Abstract

The efficient synthesis of two new stereoisomeric 3-aminocyclooctanetriols and new halocyclitol derivatives of them starting from cis,cis-1,3-cyclooctadiene are reported. Reduction of cyclooctene endoperoxide, obtained by photooxygenation of cis,cis-1,3-cyclooctadiene, with zinc yielded a cyclooctene diol followed by acetylation of the hydroxyl group, which gave dioldiacetate by OsO4/NMO oxidation. The cyclooctane dioldiacetate prepared was converted to the corresponding cyclic sulphate via the formation of a cyclic sulphite in the presence of catalytic RuO4. Reaction of this cyclic sulphate 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 cyclooctene diol with m-chloroperbenzoic acid followed by hydrolysis with HBr(g) in methanol. Treatment of bromotriol with NaN3 and the reduction of the azide group yielded the other 3-aminocyclooctanetriol desired. Hydrolysis of the epoxides with HCl(g) in methanol gave stereospecifically new chlorocyclooctanetriols.

Keywords: aminocyclitols; aminocyclooctanetriol; chlorocyclooctanetriol; cyclic sulphate; cyclitols.

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Salamci, E.; Zozik, Y. Beilstein Arch. 2020, 2020142. doi:10.3762/bxiv.2020.142.v1

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