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Synthesis of modified β-methoxyphenylalanines via diazonium chemistry and their incorporation in desoxycyclomarin analogues

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Abstract

The marine natural products cyclomarins have remarkable anti-mycobacterial and antiplasmodial activities. The heptapeptic structure of this compound class comprisis four highly interesting non-canonical amino acids, including a rather unusual syn β-methoxyphenylalanine. To get a deeper insight into the structure–activity realtionship of cyclomarines, a straightforward protocol for the stereoselective synthesis of this building block was developed, based on diazonium chemistry.

Graphical abstract: Synthesis of modified β-methoxyphenylalanines via diazonium chemistry and their incorporation in desoxycyclomarin analogues

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Publication details

The article was received on 07 Nov 2018, accepted on 30 Nov 2018 and first published on 06 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02777C
Citation: Org. Biomol. Chem., 2019, Advance Article
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    Synthesis of modified β-methoxyphenylalanines via diazonium chemistry and their incorporation in desoxycyclomarin analogues

    A. Kiefer and U. Kazmaier, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB02777C

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