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Molecules 2007, 12(8), 1890-1899; https://doi.org/10.3390/12081890

Synthesis of Novel Steroid-Peptoid Hybrid Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs)

1
Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120, Halle/Saale, Germany
2
Center for Natural Products Study, Faculty of Chemistry, University of Havana, Havana 10400, Cuba
*
Author to whom correspondence should be addressed.
Received: 24 May 2007 / Accepted: 15 August 2006 / Published: 17 August 2007
(This article belongs to the Special Issue Bile Acids)
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Abstract

Two new groups of cholane-peptoid hybrid macrocycles were produced by implementing novel combinations of the MiB methodology. Steroid-based hybrid macrolactams including heterocycle and aryl moieties were obtained by utilizing cholanic dicarboxylic acids and diamines in a bidirectional double Ugi-Four-Component (Ugi-4CR) based macrocyclization protocol. Alternatively, N-substituted cyclocholamides were produced from a cholanic pseudo-amino acid by an Ugi-4CR-based cyclooligomerization approach. Both types of macrocycles are steroid-peptoid hybrid macrocycles containing exocyclic peptidic chains. These novel frameworks are a result of the use of bile acids bifunctionalized with carboxylic and amino functionalities as bifunctional building blocks of the Ugi-MiB approach. View Full-Text
Keywords: Bile acids; macrocycles; steroids; peptoids; Ugi reaction; multicomponent reaction Bile acids; macrocycles; steroids; peptoids; Ugi reaction; multicomponent reaction
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Rivera, D.G.; Wessjohann, L.A. Synthesis of Novel Steroid-Peptoid Hybrid Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs). Molecules 2007, 12, 1890-1899.

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