title: First examples of oxidizing secondary alcohols to ketones in the presence of the disulfide functional group: synthesis of novel diketone disulfides.
abstract: The disulfide functionality is present in a number of organic compounds of interest in the fields of both chemistry and biology. Because the disulfide group is known to be highly susceptible to further oxidation by a wide range of agents, performing a chemoselective oxidation without further oxidizing the disulfide moiety poses a synthetic challenge. Reported herein are the first examples of such a chemoselective oxidation in which a series of novel secondary alcohol disulfides 2a-f have been converted to the corresponding symmetrical diketones 3a-f utilizing a modified Swern oxidation.
authors.affiliation: NitroMed, Inc., 12 Oak Park Drive, Bedford, Massachusetts 01730, USA. ffang@nitromed.com
authors.forename: X
authors.initials: X
authors.lastname: Fang
authors.forename: U K
authors.initials: UK
authors.lastname: Bandarage
authors.forename: T
authors.initials: T
authors.lastname: Wang
authors.forename: J D
authors.initials: JD
authors.lastname: Schroeder
authors.forename: D S
authors.initials: DS
authors.lastname: Garvey
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D004220:Disulfides / Q000737:chemistry; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction
chemical_list: D000438:Alcohols; D004220:Disulfides; D007202:Indicators and Reagents; D007659:Ketones