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Issue 19, 2007
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The enantioselective synthesis of APTO and AETD: polyhydroxylated β-amino acid constituents of the microsclerodermin cyclic peptides

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Abstract

The polyhydroxylated β-amino acids (2S,3R,4S,5S,7E)-3-amino-8-phenyl-2,4,5-trihydroxyoct-7-enoic acid (APTO) and (2S,3R,4S,5S,7E,9E)-3-amino-10-(4-ethoxyphenyl)-2,4,5-trihydroxydeca-7,9-dienoic acid (AETD) are key components of the microsclerodermin family of anti-fungal cyclic peptides. They have been synthesised in protected form in twelve steps using a unified strategy, with the introduction of the unsaturated sidechain in the final step of the synthesis from a common aldehyde intermediate. The synthesis features the ordered application of asymmetric aminohydroxylation and dihydroxylation reactions to efficiently introduce the stereochemistry of the targets with high selectivity.

Graphical abstract: The enantioselective synthesis of APTO and AETD: polyhydroxylated β-amino acid constituents of the microsclerodermin cyclic peptides

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Supplementary files

Article information


Submitted
24 May 2007
Accepted
26 Jul 2007
First published
17 Aug 2007

Org. Biomol. Chem., 2007,5, 3183-3189
Article type
Paper

The enantioselective synthesis of APTO and AETD: polyhydroxylated β-amino acid constituents of the microsclerodermin cyclic peptides

E. C. Shuter, H. Duong, C. A. Hutton and M. D. McLeod, Org. Biomol. Chem., 2007, 5, 3183
DOI: 10.1039/B707891A

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