Asymmetric Total Synthesis of (−)-Stemonamine and Its Stereochemical Stability

Satoshi Fujita, Keisuke Nishikawa, Takayuki Iwata, Taishi Tomiyama, Hiroshi Ikenaga, Kenji Matsumoto, Mitsuru Shindo

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The first asymmetric total synthesis of (−)-stemonamine is described. The key reactions included intramolecular acylation to construct the seven-membered ring and a tandem [2+2] cycloaddition-Dieckmann condensation reaction using an ynolate to form the fully substituted cyclopentenone moiety. Racemization and epimerization of the natural product were first experimentally demonstrated.

Original languageEnglish
Pages (from-to)1539-1543
Number of pages5
JournalChemistry - A European Journal
Volume24
Issue number7
DOIs
Publication statusPublished - Feb 1 2018

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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