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

doi:10.3390/12081890

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

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

Daniel G. Rivera¹ and Ludger A. Wessjohann^1,*

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.

Keywords: Bile acids; macrocycles; steroids; peptoids; Ugi reaction; multicomponent reaction

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MDPI and ACS Style

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.

AMA Style

Rivera DG, Wessjohann LA. Synthesis of Novel Steroid-Peptoid Hybrid Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs). Molecules. 2007; 12(8):1890-1899.

Chicago/Turabian Style

Rivera, Daniel G.; Wessjohann, Ludger A. 2007. "Synthesis of Novel Steroid-Peptoid Hybrid Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs)." Molecules 12, no. 8: 1890-1899.

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