Synthesis of Functionalized Adamantane Derivatives: (3 + 1)-Scaffolds for Applications in Medicinal and Material Chemistry

Carsten Fleck; Elisa Franzmann; Dorith Claes; Aljona Rickert; Wolfgang Maison

doi:10.1055/s-0033-1338470

Synthesis, Table of Contents

Synthesis 2013; 45(11): 1452-1461
DOI: 10.1055/s-0033-1338470

feature article

Synthesis of Functionalized Adamantane Derivatives: (3 + 1)-Scaffolds for Applications in Medicinal and Material Chemistry

Carsten Fleck

Pharmaceutical and Medicinal Chemistry, University of Hamburg, Bundesstraße 45, 20146 Hamburg, Germany Fax: +49(40)42838-3477 Email: maison@chemie.uni-hamburg.de

,

Elisa Franzmann

Pharmaceutical and Medicinal Chemistry, University of Hamburg, Bundesstraße 45, 20146 Hamburg, Germany Fax: +49(40)42838-3477 Email: maison@chemie.uni-hamburg.de

,

Dorith Claes

Pharmaceutical and Medicinal Chemistry, University of Hamburg, Bundesstraße 45, 20146 Hamburg, Germany Fax: +49(40)42838-3477 Email: maison@chemie.uni-hamburg.de

,

Aljona Rickert

Pharmaceutical and Medicinal Chemistry, University of Hamburg, Bundesstraße 45, 20146 Hamburg, Germany Fax: +49(40)42838-3477 Email: maison@chemie.uni-hamburg.de

,

Wolfgang Maison*

Pharmaceutical and Medicinal Chemistry, University of Hamburg, Bundesstraße 45, 20146 Hamburg, Germany Fax: +49(40)42838-3477 Email: maison@chemie.uni-hamburg.de

› Author Affiliations

Abstract

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Abstract

Due to its rigid cage structure, adamantane has received considerable interest as a scaffold with a defined tetrahedral geometry. In this paper we describe orthogonally functionalized tetrasubstituted adamantane derivatives. These compounds may be conjugated to other functional molecules by standard techniques such as amide formation or click chemistry and are thus useful (3 + 1) scaffolds for medicinal and material chemistry.

Key words

adamantane - multivalency - dendrimers - C ₃ symmetry - diamandoids

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References

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