Synthesis of branched carbasugars via photooxygenation and manganese(III) acetate free radical cyclization

Altun Y., Dogan S. D., BALCI M.

TETRAHEDRON, vol.70, no.33, pp.4884-4890, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 70 Issue: 33
  • Publication Date: 2014
  • Doi Number: 10.1016/j.tet.2014.05.069
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.4884-4890
  • Erciyes University Affiliated: Yes

Abstract

Transformation of cyclohexa-1,3- and 1,4-dienes to carbasugars is described. Photooxygenation of dienes gave bicyclic endoperoxides, which were reduced with thiourea to the corresponding 1,4-dials with cis-configuration. Lactonization of the remaining double bond by oxidative addition of acetic acid to the double bond in the presence of Mn(OAc)(3) followed by lactone ring-opening reaction gave the target branched carbasugars. (C) 2014 Elsevier Ltd. All rights reserved.