Synthesis of eight-membered aminocyclitol analogues

ZOZİK Y., SALAMCI E., KİLİC A.

TETRAHEDRON LETTERS, cilt.58, sa.52, ss.4822-4826, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 58 Sayı: 52
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.tetlet.2017.11.014
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.4822-4826
  • Anahtar Kelimeler: Cyclitol, Diaminocyclooctanediol, Diazidecyclooctanepoxide, Diamino-2-chlorocyclooctanol, Carbocycle, GLYCOSIDASE INHIBITORY-ACTIVITY, RNA HAIRPIN LOOPS, GLUCOSIDASE INHIBITORS, CYCLOOCTANE POLYOLS, BIOLOGICAL-ACTIVITY, EFFICIENT SYNTHESIS, ALPHA-GLUCOSIDASE, PROTO-QUERCITOL, MIMETICS, RECOGNITION
  • Atatürk Üniversitesi Adresli: Evet

Özet

The first syntheses of four stereoisomeric diaminocyclooctane diols, as well as a chlorocyclooctane aminodiol, are reported. In the first part, photooxygenation of cis,cis-1,3-cyclooctadiene gave a bicyclic endoperoxide, which was reduced with zinc followed by mesylation of the hydroxyl groups. Treatment with sodium azide afforded 1,4- and 1,2-cyclooctene diazides. Oxidation of the double bonds in the isomeric diazides with OsO4, followed by hydrogenation of the azide groups, led to 3,8-diaminocyclooctane-1,2-diol and 3,4-diaminocyclooctane-1,2-diols. In the second part, cis-3,8-diazidocyclooctene was converted into the corresponding epoxide. Stereospecific hydrolysis of the epoxide ring with HCl(g) in methanol, and hydrogenation of the azide groups gave 3,8-diamino-2-chloro-cyclooctan-l-ol. Bromination of the double bond in cyclooctene diacetate, followed by acetate deprotection, azidolysis of the bromides, and hydrogenation of the azide groups resulted in the formation of 2,3-diaminocyclooctane-1,4-diol. (C) 2017 Elsevier Ltd. All rights reserved.