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Enantioselective Synthesis of 5-LO Inhibitor Hydroxyureas. Tandem Nucleophilic Addition−Intramolecular Cyclization of Chiral Nitrones

1997; American Chemical Society; Volume: 62; Issue: 16 Linguagem: Inglês

10.1021/jo9621736

1520-6904

I. LANTOS, Joseph R. Flisak, Li Liu, Richard T. Matsuoka, Wilf Mendelson, D. E. Stevenson, Ken Tubman, Lynn Tucker, Zhang Weiyuan, Jerry L. Adams, Margaret E. Sorenson, Ravi S. Garigipati, K. Erhardt, Steve Ross,

Synthetic Organic Chemistry Methods

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.