A SYNTHESIS OF (-)-TASHIROMINE AND FORMAL SYNTHESIS OF (-TASHIROMINE UTILIZING A HIGHLY ENANTIOSELECTIVE PYRROLE())COBALOXIME PI-CATION CYCLIZATION/

Authors
GAGE JL BRANCHARD BP
Citation
Jl. Gage et Bp. Branchard, A SYNTHESIS OF (-)-TASHIROMINE AND FORMAL SYNTHESIS OF (-TASHIROMINE UTILIZING A HIGHLY ENANTIOSELECTIVE PYRROLE())COBALOXIME PI-CATION CYCLIZATION/, Tetrahedron letters, 38(40), 1997, pp. 7007-7010
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
40
Year of publication
1997
Pages
7007 - 7010
Database
ISI
SICI code
0040-4039(1997)38:40<7007:ASO(AF>2.0.ZU;2-B
Abstract
Cyclization of (5-N-pyrrolyl-2-hydroxypentyl)cobaloxime (13) proceeds by intramolecular electrophilic aromatic substitution of a cobaloxime pi-cation onto the pyrrole ring to provide 6-exo cyclization product ( 14) in 95% yield. This cyclization is highly enantioselective. It is a pplied to a synthesis of highly enantioenriched (-)-tashiromine, (-)-2 1, and a formal synthesis of (+)-tashiromine. (C) 1997 Elsevier Scienc e Ltd.