Enantioselective total synthesis of the osteoclastogenesis inhibitor (+)-symbioimine

Justin Kim*, Regan James Thomson

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

(Chemical Equation Presented) No bones about it: The first enantioselective total synthesis of the osteoclastogenesis inhibitor (+)-symbioimine (1) has been achieved. The synthesis features a convergent enol silane addition to a dimethyl acetal and a key, possibly biomimetic, intramolecular Diels-Alder reaction promoted by a dihydropyridinium ion to build four of the five requisite stereocenters in one step.

Original languageEnglish (US)
Pages (from-to)3104-3106
Number of pages3
JournalAngewandte Chemie - International Edition
Volume46
Issue number17
DOIs
StatePublished - Jun 29 2007

Keywords

  • Biomimetic synthesis
  • Cycloaddition
  • Diels-Alder reaction
  • Natural products
  • Total synthesis

ASJC Scopus subject areas

  • Chemistry(all)

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