Issue 19, 2007

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

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

Supplementary files

Article information

Article type
Paper
Submitted
24 May 2007
Accepted
26 Jul 2007
First published
17 Aug 2007

Org. Biomol. Chem., 2007,5, 3183-3189

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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