First examples of oxidizing secondary alcohols to ketones in the presence of the disulfide functional group: synthesis of novel diketone disulfides.
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.
Fang
X
X
NitroMed, Inc., 12 Oak Park Drive, Bedford, Massachusetts 01730, USA. ffang@nitromed.com
Bandarage
U K
UK
Wang
T
T
Schroeder
J D
JD
Garvey
D S
DS
D000438:Alcohols / Q000737:chemistry*; D004220:Disulfides / Q000737:chemistry; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction
D000438:Alcohols; D004220:Disulfides; D007202:Indicators and Reagents; D007659:Ketones