Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol

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SALAMCI E., Lafzi A. K.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, cilt.18, ss.1539-1543, 2022 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 18
  • Basım Tarihi: 2022
  • Doi Numarası: 10.3762/bjoc.18.163
  • Dergi Adı: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aquatic Science & Fisheries Abstracts (ASFA), Biotechnology Research Abstracts, Chemical Abstracts Core, Directory of Open Access Journals
  • Sayfa Sayıları: ss.1539-1543
  • Anahtar Kelimeler: aminocyclitols, aminocyclooctanetriol, azides, aziridines, aziridinecyclooctanediol, STEREOSPECIFIC SYNTHESIS, DL-PROTO, AMINOCYCLITOLS, AZIRIDINATION, DERIVATIVES, QUERCITOL, CONCISE, ANALOGS
  • Atatürk Üniversitesi Adresli: Evet

Özet

Cyclooctene endoperoxide was used as the key compound for the synthesis of aziridinecyclooctanediol and 3-aminocyclo-octanetriol. Reduction of the cyclooctene endoperoxide, prepared by photooxygenation of cis,cis-1,3-cyclooctadiene, with zinc gave a cyclooctenediol and then benzylation of the hydroxy group yielded dibenzylated cyclooctene. Oxidation of the latter compound by OsO4/NMO followed by mesylation of the hydroxy group provided bis(benzyloxy)cyclooctane-1,2-diyl dimethanesulfonate. Reaction of the bis(benzyloxy)cyclooctane-1,2-diyl dimethanesulfonate with NaN3 gave 2-azido-3,8-bis(benzyloxy)cyclooctyl methanesulfonate. Reduction of the azide group and debenzylation to give an amine provided the new 3-aminocyclooctanetriol. Treatment of the 2-azido-3,8-bis(benzyloxy)cyclooctyl methanesulfonate with Zn/NH4Cl and debenzylation resulted in the target aziridinecyclooctanediol.