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  Synthesis-driven mapping of the dictyodendrin alkaloids

Buchgraber, P., Domostoj, M. M., Scheiper, B., Wirtz, C., Mynott, R., Rust, J., et al. (2009). Synthesis-driven mapping of the dictyodendrin alkaloids. Tetrahedron, 65(33), 6519-6534. doi:10.1016/j.tet.2009.06.058.

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 Creators:
Buchgraber, Philipp1, Author           
Domostoj, Mathias M.1, Author           
Scheiper, Bodo1, Author           
Wirtz, Cornelia2, Author           
Mynott, Richard2, Author           
Rust, Jörg3, Author           
Fürstner, Alois1, Author           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445627              
3Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Free keywords: Alkaloids; DNA; Gold; Indoles; Telomerase; Titanium
 Abstract: The dictyodendrin alkaloids have been described as the first telomerase inhibitors of marine origin. As such they represent interesting lead compounds in the quest for small molecule inhibitors of this tumor-marker enzyme. Described herein is the preparation of a collection of dictyodendrin-like compounds that hinges on the formation of their indole subunit by reductive cyclization of appropriate keto-amide precursors mediated by low valent titanium. It is shown that the underlying concept can be extended from the synthesis of heterocycles to the preparation of phenol and aniline derivatives using oxo-acid, oxo-nitrile or oxo-lactam derivatives as the substrates; such arene formations can even be carried out in cascade. Exploratory studies into the closure of the B-ring of the dictyodendrins with the aid of electrophilic reagents such as Ph3PAuCl/AgSbF6 or I+ revealed the bias of these polycyclic heteroarenes to undergo unusual skeletal rearrangements. It is demonstrated that the individual dictyodendrins and analogues are capable of cleaving double stranded DNA under oxidative conditions, provided that they exhibit at least one unprotected phenol group in their periphery.

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Language(s): eng - English
 Dates: 2009-06-152009-03-172009-06-152009-06-212009-08-15
 Publication Status: Published in print
 Pages: 16
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: eDoc: 460262
DOI: 10.1016/j.tet.2009.06.058
ISI: 000268645600008
 Degree: -

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Title: Tetrahedron
  Other : Tetrahedron
Source Genre: Journal
 Creator(s):
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Publ. Info: Oxford : Pergamon
Pages: - Volume / Issue: 65 (33) Sequence Number: - Start / End Page: 6519 - 6534 Identifier: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/954925448773