NDLI: Biology-Oriented Combined Solid- and Solution-Phase Synthesis of a Macroline-Like Compound Collection

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Biology-Oriented Combined Solid- and Solution-Phase Synthesis of a Macroline-Like Compound Collection

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Biology-Oriented Combined Solid- and Solution-Phase Synthesis of a Macroline-Like Compound Collection

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Nören-müller, Andrea Wilk, Wolfram Kaiser, Markus Waldmann, Herbert
Description	Author Affiliation: Wilk W ( Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany.)
Abstract	Macrolines constitute a class of natural products that has more than 100 members and displays diverse biological activities. These compounds feature a cycloocta[b]indole scaffold that represents an interesting target structure for biology-oriented synthesis (BIOS). We have presented a solid-phase synthesis of isomerically pure cycloocta[b]indoles by employing the Pictet–Spengler reaction and the Dieckmann cyclization as key steps. The scope of this reaction sequence was investigated in more detail by using various additional diversification procedures, such as Pd-catalyzed Sonogashira or Suzuki couplings on a solid phase, thus allowing, for example, the generation of 10-substituted cycloocta[b]indole derivatives. Finally, solution-phase decoration of the cycloocta[b]indole skeleton by reduction and saponification was evaluated, thereby further extending the scope of the solid-phase synthesis.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	44
Volume Number	15
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2009-11-09
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Indole Alkaloids Chemical Synthesis Chemistry Indoles Stereoisomerism Substrate Specificity Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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