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

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

1 and 1,*
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 Bile acids; macrocycles; steroids; peptoids; Ugi reaction; multicomponent reaction
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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