Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, cilt.17, ss.705-710, 2021 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 17
- Basım Tarihi: 2021
- Doi Numarası: 10.3762/bjoc.17.59
- 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.705-710
- Anahtar Kelimeler: aminocyclitols, aminocyclooctanetriol, chlorocyclooctanetriol, cyclic sulfate, cyclitols, GLYCOSIDASE INHIBITORY-ACTIVITY, EFFICIENT SYNTHESIS, DL-PROTO, AMINOCYCLITOLS, CYCLOADDITION, VALIENAMINE, QUERCITOL, CONCISE, GALA
- Atatürk Üniversitesi Adresli: Evet
Özet
The efficient synthesis of two new stereoisomeric 3-aminocyclooctanetriols and their new halocyclitol derivatives 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 hydroxy group, which gave dioldiacetate by OsO4/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 RuO4. 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 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 desired 3-aminocyclooctanetriol. Hydrolysis of the epoxides with HCl(g) in methanol gave stereospecifically new chlorocyclooctanetriols.