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

Baran A., Secen H., Balci M.

SYNTHESIS-STUTTGART, no.10, pp.1500-1502, 2003 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2003
  • Doi Number: 10.1055/s-2003-40517
  • Journal Name: SYNTHESIS-STUTTGART
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1500-1502
  • Middle East Technical University Affiliated: No

Abstract

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%).