title: Asymmetric syntheses of APTO and AETD: the β-amino acid fragments within microsclerodermins C, D, and E.
abstract: 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.
authors: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.
authors: Stephen G
authors: SG
authors: Davies
authors: Ai M
authors: AM
authors: Fletcher
authors: Emma M
authors: EM
authors: Foster
authors: James A
authors: JA
authors: Lee
authors: Paul M
authors: PM
authors: Roberts
authors: James E
authors: JE
authors: Thomson
mesh_terms: D021542:Amino Acids, Neutral / Q000138:chemical synthesis* / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D021542:Amino Acids, Neutral; D010446:Peptide Fragments; D010456:Peptides, Cyclic; C528588:microsclerodermin C; C528589:microsclerodermin D; C486898:microsclerodermin E; D008094:Lithium