Synthesis and Characterization of Novel Aryl Cyclitols: Polycyclitols

BALCI N., ANIL B., Kelebekli L., ŞAHİN E., GÖKSU S.

SYNTHETIC COMMUNICATIONS, cilt.43, sa.22, ss.3054-3063, 2013 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 43 Sayı: 22
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1080/00397911.2013.767347
  • Dergi Adı: SYNTHETIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3054-3063
  • Atatürk Üniversitesi Adresli: Evet

Özet

New polycyclitols were synthesized starting from 1,4-naphthoquinone. An endo-selective Diels-Alder cycloaddition between 1,4-naphthoquinone and 1-acetoxybutadiene afforded a diketone. Reduction of the diketone with a NaBH4-CeCl(3)7H(2)O system gave a new cyclitol analog diol acetate. Acetylation of this compound afforded a triacetate. Oxidation of the double bond of the triacetate compound with OsO4 followed by acetylation of hydroxyl groups gave the pentaacetate, whose structure was established unequivocally via application of x-ray crystallographic methods. Hydrolysis of ester groups of pentaacetate under basic condutions furnished the desired and another novel aryl cyclitol.