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

Jennifer L. Gage, Bruce Branchaud

Research output: Contribution to journalArticle

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Abstract

Cyclization of (5-N-pyrrolyl-2-hydroxypentyl)cobaloxime (13) proceeds by intramolecular electrophilic aromatic substitution of a cobaloxime π-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.

Original languageEnglish (US)
Pages (from-to)7007-7010
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number40
DOIs
Publication statusPublished - Oct 6 1997
Externally publishedYes

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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