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

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Abstract

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.

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  • Organic Chemistry
Original languageEnglish
Pages (from-to)6083-6085
JournalTetrahedron Letters
Volume45
Issue number31
Publication statusPublished - 2004
Publication categoryResearch
Peer-reviewedYes

Bibliographic note

The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)