461644-55-3Relevant academic research and scientific papers
Stereoselective synthesis of oxazolidin-2-ones via an asymmetric aldol/curtius reaction: Concise total synthesis of (?)-cytoxazone
Choi, Hosam,Choi, Joohee,Jang, Hanho,Lee, Kiyoun
supporting information, (2021/06/14)
Herein, we are reporting an efficient approach toward the synthesis of 4,5-disubstituted oxazolidin-2-one scaffolds. The developed approach is based on a combination of an asymmetric aldol and a modified Curtius protocol, which uses an effective intramolecular ring closure to rapidly access a range of oxazolidin-2-one building blocks. This strategy also permits a straightforward and concise asymmetric total synthesis of (?)-cytoxazone. Consisting of three steps, this is one of the shortest syntheses reported to date. Ultimately, this convenient platform would provide a promising method for the early phases of drug discovery.
Auxiliary strategies for the preparation of β-amino alcohols with reductive cross-coupling and a synthesis of (-)-cytoxazone
Lin, Xiangjie,Bentley, Paul A.,Xie, Hexin
, p. 7849 - 7852 (2007/10/03)
Imine auxiliaries including chiral N-tert-butanesulfinyl imines have been successfully utilized to provide stereochemical control to the reductive cross-coupling of imines with aldehydes or ketones. This methodology has been applied to the synthesis of (-)-cytoxazone.
A new synthesis of cytoxazone and its diastereomers provides key initial SAR information
Carter, Percy H.,LaPorte, Jacob R.,Scherle, Peggy A.,Decicco, Carl P.
, p. 1237 - 1239 (2007/10/03)
A short, enantioselective, and diastereoselective synthesis of cytoxazone, a Th2-selective immunomodulator from Streptomyces, is described. The route was readily adapted to the synthesis of the three other stereoisomers of natural cytoxazone. Evaluation of these compounds revealed that the stereochemical configuration of the oxazolidinone ring did not influence their biological activity.
Stereoselective synthesis of (-)-cytoxazone
Carda, Miguel,Gonzalez, Florenci,Sanchez, Richard,Marco
, p. 1005 - 1010 (2007/10/03)
The stereoselective synthesis of the cytokine modulator (-)-cytoxazone in enantiopure form is described. Key steps of the process are a syn-stereoselective aldol addition of a chiral ketone mediated by chlorodicyclohexylborane, and a Curtius rearrangement
