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A synthesis of (−)-tashiromine and formal synthesis of (+)-tashiromine utilizing a highly enantioselective pyrrole/cobaloxime π-cation cyclization

✍ Scribed by Jennifer L Gage; Bruce P Branchaud

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
285 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

Cyclization of (5-N-pyrrolyl-2-hydroxypentyl)cobaloxime ( 13) proceeds by intramolecular electrophilic aromatic substitution of a cobaloxime g-cation onto the pyrrole ring to provide 6-exo cyclization product ( 14) in 95% yield. This cyclization is highly enantioselective. It is applied to a synthesis of highly enantioenriched (-)-tashiromine, (-)-21, and a formal synthesis of (+)-tashiromine.

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