A new synthon for the synthesis of aminoinositol derivatives

Cokol N. K., Kaya S., BALCI M.

TETRAHEDRON LETTERS, vol.58, no.28, pp.2732-2735, 2017 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 58 Issue: 28
  • Publication Date: 2017
  • Doi Number: 10.1016/j.tetlet.2017.05.099
  • Journal Name: TETRAHEDRON LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2732-2735
  • Keywords: Oxabicycloheptene, Aminoinositol, Diacylazide, Curtius rearrangement, Neighbouring group participation, RING-OPENING REACTIONS, DIELS-ALDER REACTIONS, STEREOSPECIFIC SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, BRANCHED CARBASUGARS, ACID, AMINOCYCLITOL, CONSTRUCTION, CATALYST, ANALOGS
  • Middle East Technical University Affiliated: Yes

Abstract

The regio- and stereoselective synthesis of a new synthon, trans-3,8-dioxatricyclo[3.2.1.0(2,4)]octane-6,7-diamine, from 7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate is reported. Transformation of the acid functionalities to acyl azides followed by Curtius rearrangement gave the corresponding trans-diisocyanate, which was reacted with HCl to produce a trans-diamino compound that is a potentially important synthon for the versatile synthesis of aminocyclitols. (C) 2017 Elsevier Ltd. All rights reserved.