Stereospecific synthesis of a new class of aminocyclitol with the conduramine D-2 configuration

Kelebekli L., Celik M., Sahin E., Kara Y., Balci M.

TETRAHEDRON LETTERS, vol.47, no.39, pp.7031-7035, 2006 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 47 Issue: 39
  • Publication Date: 2006
  • Doi Number: 10.1016/j.tetlet.2006.07.108
  • Journal Name: TETRAHEDRON LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.7031-7035
  • Keywords: cyclitols, aminocyclitol, endoperoxide, bicyclic aliphatic, compounds, oxidation, X-ray analysis, GLYCOSIDASE INHIBITORY-ACTIVITY, RING-CLOSING METATHESIS, ENANTIOMERICALLY PURE, RADICAL CYCLIZATION, CONDURITOL ANALOGS, D-GLUCOSE, CARBASUGAR, EFFICIENT, POLYCYCLITOLS, CARBOCYCLES
  • Middle East Technical University Affiliated: No

Abstract

A new aminocyclitol derived from bicyclo[4.2.0(1,6)]octane was synthesized starting from cyclooctatetraene. Photooxygenation of trans-7,8-diacetoxy-bicyclo[4.2.0]octa-2,4-diene afforded a bicyclic endoperoxide. Reduction of the endoperoxide with thiourea followed by a palladium-catalyzed ionization/cyclization reaction gave an oxazolidinone derivative. Oxidation of the double bond in the oxazolidinone with KNlnO(4) followed by acetylation gave the oxazolidinone-tetraacetate whose exact configuration was determined by X-ray diffraction analysis. Hydrolysis of the oxazolidinone ring and removal of the acetate groups furnished the desired aminocyclitol. (c) 2006 Elsevier Ltd. All rights reserved.