Synthesis and conformational analysis of 9,10-bis-aminomethyl-11,12-dicarboxy-dibenzobarrelene derivatives
Författare
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.
Avdelning/ar
Publiceringsår
2004
Språk
Engelska
Sidor
6083-6085
Publikation/Tidskrift/Serie
Tetrahedron Letters
Volym
45
Issue
31
Dokumenttyp
Artikel i tidskrift
Förlag
Elsevier
Ämne
- Organic Chemistry
Status
Published
ISBN/ISSN/Övrigt
- ISSN: 0040-4039