Solid-phase synthesis of optically active substituted 2 aminofuranones using an activated carbonate linker

Dimitris Matiadis; Kyriakos C Prousis; Olga Igglessi-Markopoulou

doi:10.3390/molecules14103914

Solid-phase synthesis of optically active substituted 2 aminofuranones using an activated carbonate linker

Molecules. 2009 Sep 30;14(10):3914-21. doi: 10.3390/molecules14103914.

Authors

Dimitris Matiadis¹, Kyriakos C Prousis, Olga Igglessi-Markopoulou

Affiliation

¹ Laboratory of Organic Chemistry, School of Chemical Engineering, National Technical University of Athens, Zografou Campus, Athens 15773, Greece.

Abstract

An efficient three-step solid-phase synthesis of diverse 3,5-disubstituted-2-aminofuranones has been developed. alpha-Hydroxy acids loaded on a nitrophenyl carbonate derivative of Wang resin are used as acylating agents for the C-acylation of active methylene compounds and the resulting intermediates provided, through a cyclative cleavage reaction, the desired product.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acylation
Carbonates / chemistry
Furans / chemical synthesis*
Furans / chemistry
Hydroxy Acids / chemistry
Polystyrenes / chemistry

Substances

Carbonates
Furans
Hydroxy Acids
Polystyrenes
Wang resin