Synthesis of a new class of aminocyclitol analogues with the conduramine D-2 configuration

KELEBEKLI L., KARA Y., ÇELİK M.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, cilt.6, 2010 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 6
  • Basım Tarihi: 2010
  • Doi Numarası: 10.3762/bjoc.6.15
  • Dergi Adı: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Anahtar Kelimeler: aminocyclitol, cyclitols, endoperoxide, oxidation, X-ray analysis, RING-CLOSING METATHESIS, STEREOSPECIFIC SYNTHESIS, GLYCOSIDASE INHIBITORS, ENANTIOSELECTIVE SYNTHESIS, CHEMOTHERAPEUTIC VALUE, CONDURITOLS, CARBASUGARS
  • Atatürk Üniversitesi Adresli: Evet

Özet

A new class of aminocyclitol derivatives with the bicyclo[4.2.0] octane skeleton was synthesized starting from cyclooctatetraene. Photooxygenation of trans-7,8-diacetoxy- and cis-7,8-dichlorobicyclo[4.2.0]octa-2,4-diene afforded the bicyclic endoperoxides. Reduction of the latter with thiourea followed by a Pd(0) catalyzed ionization/cyclization reaction gave the corresponding oxazolidinone derivatives. Oxidation of the double bond with KMnO4 or OsO4 followed by acetylation gave the acetate derivatives, the exact configuration of which was determined by spectroscopic methods. Hydrolysis of the oxazolidinone rings and removal of the acetate groups furnished the desired aminocyclitols.