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Efficient asymmetric syntheses of APTO and AETD, the highly functionalized β-amino acid fragments within microsclerodermins C, D, and E, are reported. The conjugate addition of lithium (R)-N-benzyl-N-(α-methylbenzyl)amide to tert-butyl (E,E)-7-(triisopropylsilyloxy)hepta-2,4-dienoate and in situ enolate oxidation with (-)-camphorsulfonyloxaziridine, diastereoselective dihydroxylation of a 2,3-syn-γ,δ-unsaturated-α-hydroxy-β-amino ester derivative under Donohoe conditions, and a Julia-Kocieński olefination were used as the key steps.

Original publication

DOI

10.1021/jo302731m

Type

Journal article

Journal

J Org Chem

Publication Date

15/03/2013

Volume

78

Pages

2500 - 2510

Keywords

Amino Acids, Neutral, Lithium, Molecular Structure, Oxidation-Reduction, Peptide Fragments, Peptides, Cyclic, Stereoisomerism