A new synthon for the synthesis of aminoinositol derivatives
TETRAHEDRON LETTERS, vol.58, no.28, pp.2732-2735, 2017 (SCI-Expanded, Scopus)
- 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.