Studies toward a marine toxin immunogen: Enantioselective synthesis of the spirocyclic imine of (-)-gymnodimine

Ke Kong, Ziad Moussa, Daniel Romo

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

(Chemical Equation Presented) An enantioselective Diels-Alder reaction catalyzed by an Evans' copper-bis(oxazoline) complex was utilized to construct a highly functionalized spirolactam, a key intermediate in our projected total synthesis of the marine toxin, gymnodimine. Additional transformations, including a mild N-tosyl group deprotection, afforded a keto spirocyclic imine moiety, the proposed pharmacophore of gymnodimine. Thus, the prepared ketone is a potentially useful intermediate for conjugation to provide an immunogen for eventual monitoring of gymnodimine and congeners.

Original languageEnglish
Pages (from-to)5127-5130
Number of pages4
JournalOrganic Letters
Volume7
Issue number23
DOIs
Publication statusPublished - Nov 10 2005
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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