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

Grundberg, Hans LU ; Wendt, Ola LU and Nilsson, Ulf LU (2004) In Tetrahedron Letters 45(31). p.6083-6085
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... (More)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron Letters
volume
45
issue
31
pages
6083 - 6085
publisher
Elsevier
external identifiers
  • wos:000222829600035
  • scopus:3142769800
ISSN
0040-4039
DOI
10.1016/j.tetlet.2004.04.197
language
English
LU publication?
yes
id
61cb5732-25fa-4276-8553-7f1cbd6c5c4c (old id 141219)
date added to LUP
2007-07-10 10:44:57
date last changed
2017-01-01 07:23:32
@article{61cb5732-25fa-4276-8553-7f1cbd6c5c4c,
  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.},
  author       = {Grundberg, Hans and Wendt, Ola and Nilsson, Ulf},
  issn         = {0040-4039},
  language     = {eng},
  number       = {31},
  pages        = {6083--6085},
  publisher    = {Elsevier},
  series       = {Tetrahedron Letters},
  title        = {Synthesis and conformational analysis of 9,10-bis-aminomethyl-11,12-dicarboxy-dibenzobarrelene derivatives},
  url          = {http://dx.doi.org/10.1016/j.tetlet.2004.04.197},
  volume       = {45},
  year         = {2004},
}