Synthesis and conformational analysis of 9,10-bis-aminomethyl-11,12-dicarboxy-dibenzobarrelene derivatives

Summary, in English

The synthesis of bis-gamma-amino acid dibenzobarrelene derivatives (9,10-bis-aminomethyl-11,12-bis-carboxy-dibenzobarrelene) is presented. Bromomethylation of anthracene followed by azide substitution gave 9,10-bis-azidomethylanthracene. Azide reduction, N-Boc protection, and Diels-Alder cycloaddition in DMAD furnished the protected 9,10-bis-aminomethyl-11,12-dicarboxy-dibenzobarrelene derivative, which was further converted into the bis-gamma-amino acid methyl ester, the N-Boc-protected bis-gamma-amino methyl amide, and a bis-gamma-lactam. Monte Carlo simulations and X-ray analysis of the 9,10-substituted dibenzobarrelenes revealed an exposed hydrophobic surface surrounded by amino and carboxy groups. (C) 2004 Elsevier Ltd. All rights reserved.

• Author: Hans Grundberg; Ola Wendt; Ulf Nilsson
• Department/s: Centre for Analysis and Synthesis
• Publishing year: 2004
• Language: English
• Pages: 6083-6085
• Publication/Series: Tetrahedron Letters
• Volume: 45
• Issue: 31
• Links: http://dx.doi.org/10.1016/j.tetlet.2004.04.197
• Document type: Journal article
• Publisher: Elsevier
• Topic: Organic Chemistry
• Status: Published
• ISBN/ISSN/Other: ISSN: 0040-4039