Synthesis of cycloheptane-1,2,3,4-tetraols as cyclitol mimetics

Senguel M. E., Menzek A., SARAÇOĞLU N.

JOURNAL OF CHEMICAL RESEARCH, no.6, pp.382-384, 2005 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2005
  • Doi Number: 10.3184/0308234054506794
  • Journal Name: JOURNAL OF CHEMICAL RESEARCH
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC), Current Chemical Reactions (CCR)
  • Page Numbers: pp.382-384
  • Ankara University Affiliated: No

Abstract

Acidic hydrolysis and acetylation of epoxidation products 11a/b of 1,4-diacetoxy-2-cycloheptene afforded unsymmetrical 1,2,3,4-tetraacetoxycycloheptane (12). OsO4-cis-hydroxylation and acetylation of 1,4-diacetoxy-2-cycloheptene gave two symmetrical 1,2,3,4-tetraacetoxycycloheptanes (14/15). Deacetylation of 1,2,3,4-tetraacetoxy cycloheptanes gave cycloheptane-1,2,3,4-tetraols as cyclitol mimetics.