Enantioselective synthesis of a 5-LO inhibiting hydroxyurea. Construction of the dihydro-benzofuran nucleus by tandem nucleophilic addition and intramolecular cyclization
- Resource Type
- Article
- Authors
- Flisak, Joseph R.; Lantos, Ivan; Liu, Li; Matsuoka, Richard T.; Mendelson, Wilford L.; Tucker, Lynn M.; Villani, Anthony J.; Zhang, Wei-Yuan
- Source
- Tetrahedron Letters; January 1996, Vol. 37 Issue: 27 p4639-4642, 4p
- Subject
- Language
- ISSN
- 00404039
An enantioselective synthesis of a 5-LO inhibiting chiral hydroxyurea is described based on the nucleophilic addition of dimethylsulfoxonium ylide to a nitrone bearing a mannose-derived chiral auxiliary. The dihydrobenzofuran skeleton is then constructed by a spontaneous cyclization of the initial adduct, thus completing a tandem nucleophilic addition-cyclization protocol.