ENANTIOSELECTIVE SYNTHESIS OF A 5-LO INHIBITING HYDROXYUREA - CONSTRUCTION OF THE DIHYDRO-BENZOFURAN NUCLEUS BY TANDEM NUCLEOPHILIC-ADDITION AND INTRAMOLECULAR CYCLIZATION

Authors
FLISAK JR LANTOS I LIU L MATSUOKA RT MENDELSON WL TUCKER LM VILLANI AJ ZHANG WY
Citation
Jr. Flisak et al., ENANTIOSELECTIVE SYNTHESIS OF A 5-LO INHIBITING HYDROXYUREA - CONSTRUCTION OF THE DIHYDRO-BENZOFURAN NUCLEUS BY TANDEM NUCLEOPHILIC-ADDITION AND INTRAMOLECULAR CYCLIZATION, Tetrahedron letters, 37(27), 1996, pp. 4639-4642
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
27
Year of publication
1996
Pages
4639 - 4642
Database
ISI
SICI code
0040-4039(1996)37:27<4639:ESOA5I>2.0.ZU;2-L
Abstract
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 di hydrobenzofuran skeleton is then constructed by a spontaneous cyclizat ion of the initial adduct, thus completing a tandem nucleophilic addit ion-cyclization protocol. Copyright (C) 1996 Elsevier Science Ltd