Tetrahedron Letters p. 4639 - 4642 (1996)
Update date:2022-07-30
Topics:
Flisak, Joseph R.
Lantos, Ivan
Liu, Li
Matsuoka, Richard T.
Mendelson, Wilford L.
Tucker, Lynn M.
Villani, Anthony J.
Zhang, Wei-Yuan
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.
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