Synthesis and conformational analysis of 9,10-bis-aminomethyl-11,12-dicarboxy-dibenzobarrelene derivatives
(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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/141219
- author
- Grundberg, Hans LU ; Wendt, Ola LU and Nilsson, Ulf LU
- organization
- publishing date
- 2004
- 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
- additional info
- 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)
- id
- 61cb5732-25fa-4276-8553-7f1cbd6c5c4c (old id 141219)
- date added to LUP
- 2016-04-01 17:04:36
- date last changed
- 2022-01-29 00:11:57
@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}},
doi = {{10.1016/j.tetlet.2004.04.197}},
volume = {{45}},
year = {{2004}},
}