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

8 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

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Acylation
Condensation reactions
Cycloaddition
Biological Products
stemonamine
cyclopentenone

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

Asymmetric Total Synthesis of (−)-Stemonamine and Its Stereochemical Stability. / Fujita, Satoshi; Nishikawa, Keisuke; Iwata, Takayuki; Tomiyama, Taishi; Ikenaga, Hiroshi; Matsumoto, Kenji; Shindo, Mitsuru.

In: Chemistry - A European Journal, Vol. 24, No. 7, 01.02.2018, p. 1539-1543.

Research output: Contribution to journalArticle

Fujita, Satoshi ; Nishikawa, Keisuke ; Iwata, Takayuki ; Tomiyama, Taishi ; Ikenaga, Hiroshi ; Matsumoto, Kenji ; Shindo, Mitsuru. / Asymmetric Total Synthesis of (−)-Stemonamine and Its Stereochemical Stability. In: Chemistry - A European Journal. 2018 ; Vol. 24, No. 7. pp. 1539-1543.
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