Coniferin and Derivatives: a Fast and Easy Synthesis via the Aldehyde Series Using Phase-Transfer Catalysis

Nicolas Daubresse; Charlette Francesch; Farida Mhamdi; Christian Rolando

doi:10.1055/s-1998-2009

Synthesis 1998; 1998(2): 157-161
DOI: 10.1055/s-1998-2009

paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Coniferin and Derivatives: a Fast and Easy Synthesis via the Aldehyde Series Using Phase-Transfer Catalysis

Nicolas Daubresse^* , Charlette Francesch, Farida Mhamdi, Christian Rolando

^*Ecole Normale Supérieure, Département de Chimie, URA 1679 du CNRS, Processus d'Activation Móleculaire, 24 rue Lhomond, 75231 Paris Cedex 05, France; Fax + 33(1)44 32 34 65; E-mail: chr@roxane.ens.fr

Abstract

als PDF herunterladen Alle Artikel dieser Rubrik

Coniferin was synthesised in good yields (56% starting from vanillin) under mild conditions. A one-pot coupling of the glucosidation and Wittig-type reactions led to coniferaldehyde tetra-O-acetylglucoside, easily reduced into tetra-O-acetylconiferin by sodium borohydride. Similar procedures were used for the synthesis of syringin and the glucoside of 4-coumaryl alcohol.

coniferin - lignin - phase transfer - syringin - Wittig

PDF (50 kb)