An efficient and highly stereoselective synthesis of gala-Quercitol from 1,4-cyclohexadiene

BARAN A., Secen H., BALCI M.

SYNTHESIS-STUTTGART, sa.10, ss.1500-1502, 2003 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2003
  • Doi Numarası: 10.1055/s-2003-40517
  • Dergi Adı: SYNTHESIS-STUTTGART
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1500-1502
  • Atatürk Üniversitesi Adresli: Evet

Özet

gala-Quercitol was synthesized from 1,4-cyclohexadiene in seven steps and overall yield of 68%. Reaction of 5,6-dibromo-2,2-dimethylhexahydro-1,3-benzodioxole, synthesized from 1,4-cyclohexadiene in three steps, with excess NaOMe gave (3aalpha,5alpha,7aalpha)-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole. cis-Hydroxylation of the benzodioxole followed by acetylation with AcCl gave 5-O-methyl-gala-quercitol tetraacetate from which gala-quercitol was obtained by hydrolysis and demethylation with aq HBr (47%).