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Issue 18, 2018
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Total synthesis of the natural HDAC inhibitor Cyl-1

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Abstract

Chelate enolate Claisen rearrangements are powerful reactions for constructing amino acid scaffolds. They generally proceed via chair-like transition states with excellent transfer of stereogenic information. Utilizing this reaction in natural product synthesis gives access to non-proteinogenic amino acids such as (2S,9S)-2-amino-8-oxo-9,10-epoxydecanoic acid (Aoe), the unusual amino acid of a series of histone deacetylase inhibitors (HDACi). Herein the first total synthesis of Cyl-1, a cyclotetrapeptide from Cylindrocladium scoparium, is described.

Graphical abstract: Total synthesis of the natural HDAC inhibitor Cyl-1

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Publication details

The article was received on 14 Feb 2018, accepted on 16 Mar 2018 and first published on 24 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00391B
Citation: Org. Biomol. Chem., 2018,16, 3464-3472
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    Total synthesis of the natural HDAC inhibitor Cyl-1

    P. Servatius and U. Kazmaier, Org. Biomol. Chem., 2018, 16, 3464
    DOI: 10.1039/C8OB00391B

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