Efficient and shortcut syntheses of some novel eight-membered ring cyclitols starting from cycloocta-1,3-diene

ECER K., SALAMCI E.

TETRAHEDRON, cilt.70, sa.44, ss.8389-8396, 2014 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 70 Sayı: 44
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1016/j.tet.2014.08.060
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.8389-8396
  • Anahtar Kelimeler: Cyclitol, 3-Aminocyclooctanetriol, Cyclooctanetetraol, 3-Chlorocyclooctanetriol, Endoperoxide, Carbasugar, BASE-CATALYZED DECOMPOSITION, GLYCOSIDASE INHIBITORS, STEREOSELECTIVE-SYNTHESIS, ALKYL HYDROPEROXIDES, BIOLOGICAL-ACTIVITY, GAS-PHASE, D-GLUCOSE, DL-PROTO, CHEMISTRY, CARBASUGAR
  • Atatürk Üniversitesi Adresli: Evet

Özet

Cyclooctane-1,2,3,4-tetraols, aminocyclooctanetriol, and chlorocyclooctanetriol were synthesized starting from cis,cis-1,3-cyclooctadiene by a concise and efficient method. Cyclooctene endoperoxide and cyclooctene epoxide obtained by photooxygenation and epoxidation, respectively, of cis,cis-1,3-cyclooctadiene were used as the key intermediates. The other oxygen, nitrogen, and chloro functionalities were introduced via epoxidation of the remaining double bond, ring-opening of epoxide, and cis-hydroxylation reactions. (C) 2014 Elsevier Ltd. All rights reserved.Cyclooctane-1,2,3,4-tetraols, aminocyclooctanetriol, and chlorocyclooctanetriol were synthesized starting from cis,cis-1,3-cyclooctadiene by a concise and efficient method. Cyclooctene endoperoxide and cyclooctene epoxide obtained by photooxygenation and epoxidation, respectively, of cis,cis-1,3-cyclooctadiene were used as the key intermediates. The other oxygen, nitrogen, and chloro functionalities were introduced via epoxidation of the remaining double bond, ring-opening of epoxide, and cis-hydroxylation reactions. (C) 2014 Elsevier Ltd. All rights reserved.Cyclooctane-1,2,3,4-tetraols, aminocyclooctanetriol, and chlorocyclooctanetriol were synthesized starting from cis,cis-1,3-cyclooctadiene by a concise and efficient method. Cyclooctene endoperoxide and cyclooctene epoxide obtained by photooxygenation and epoxidation, respectively, of cis,cis-1,3-cyclooctadiene were used as the key intermediates. The other oxygen, nitrogen, and chloro functionalities were introduced via epoxidation of the remaining double bond, ring-opening of epoxide, and cis-hydroxylation reactions. (C) 2014 Elsevier Ltd. All rights reserved.