Wilk, Wolfram; Nören-Müller, Andrea; Kaiser, Markus; Waldmann, Herbert:
Biology-Oriented Combined Solid- and Solution-Phase Synthesis of a Macroline-Like Compound Collection
2009
In: Chemistry, Jg. 15 (2009), Heft 44, S. 11976 - 11984
Artikel/Aufsatz in Zeitschrift2009Biologie
Titel:
Biology-Oriented Combined Solid- and Solution-Phase Synthesis of a Macroline-Like Compound Collection
Autor(in):
Wilk, Wolfram; Nören-Müller, Andrea; Kaiser, MarkusLSF; Waldmann, Herbert
Erscheinungsjahr
2009
WWW URL
Erschienen in:
Titel:
Chemistry
in:
Jg. 15 (2009), Heft 44, S. 11976 - 11984
ISSN:
Signatur der UB

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.