title: A Linchpin Synthesis of 6-Hydroxyceramides from Aziridine Aldehydes.
abstract: A chemoselective N-oxidation/Meisenheimer rearrangement protocol was developed to generate vinylaziridine scaffolds from aziridine aldehydes. A subsequent Lewis acid-mediated aziridine ring opening with carboxylic acid nucleophiles followed by N-O bond cleavage furnishes a human skin 6-hydroxyceramide natural product in short order. The utility of this methodology is demonstrated by the preparation of a number of unnatural 6-hydroxyceramide analogues. This modular approach enables the expedient synthesis of poorly understood skin lipids, which may find application in therapeutics and cosmetics.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, ON M5S 3H6, Canada.
authors.forename: Sean K
authors.initials: SK
authors.lastname: Liew
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, ON M5S 3H6, Canada.
authors.forename: Sherif J
authors.initials: SJ
authors.lastname: Kaldas
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, ON M5S 3H6, Canada.
authors.forename: Andrei K
authors.identifier: 0000-0003-3170-9103
authors.initials: AK
authors.lastname: Yudin