191280-99-6Relevant academic research and scientific papers
Enantioselective Synthesis of 5-LO Inhibitor Hydroxyureas. Tandem Nucleophilic Addition-Intramolecular Cyclization of Chiral Nitrones
Lantos, Ivan,Flisak, Joseph,Liu, Li,Matsuoka, Richard,Mendelson, Wilf,Stevenson, David,Tubman, Ken,Tucker, Lynn,Zhang, Wei-Yuan,Adams, Jerry,Sorenson, Margaret,Garigipati, Ravi,Erhardt, Karl,Ross, Steve
, p. 5385 - 5391 (2007/10/03)
An enantioselective synthesis of chiral hydroxyurea based 5-lipoxygenase inhibitors is reported via a five-step sequence in about 30% overall yield. The synthesis is based on a novel tandem nucleophilic addition-intramolecular cyclization reaction in which a chiral nitrone functions as the electrophilic acceptor species. A mannose-based chiral auxiliary controls the diastereoselectivity of the reaction in an 8:1 ratio. After the auxiliary removal and appropriate functionalization, a single recrystallization afforded the target structures in >99% ee.
