The First Enantioselective Total Synthesis of (-)-Trans-Dihydronarciclasine

Gábor Varró, L. Hegedûs, András Simon, Attila Balogh, A. Grün, Ibolya Leveles, B. Vértessy, István Kádas

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A feasible and enantioselective total synthesis of (-)-Trans-dihydronarciclasine [(-)-1], a highly biologically active alkaloid, was devised starting from vanillin (8). The key step of this new synthesis was an asymmetric, organocatalytic Michael addition, in which an optically active nitropentanone [(-)-13] was obtained from a butenone derivative (12). Excellent enantioselectivity (>99% ee) was achieved using the (8S,9S)-9-Amino(9-deoxy)epiquinine (16) organocatalyst. The target molecule can be prepared in 13 steps from compound (-)-13. The total synthesis has provided a facile and first access to the ent-form of naturally occurring (+)-Trans-dihydronarciclasine, a highly potent cytostatic alkaloid.

Original languageEnglish
Pages (from-to)1909-1917
Number of pages9
JournalJournal of Natural Products
Volume80
Issue number6
DOIs
Publication statusPublished - Jun 23 2017

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Alkaloids
Cytostatic Agents
Enantioselectivity
Derivatives
Molecules
dihydronarciclasine
vanillin

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

The First Enantioselective Total Synthesis of (-)-Trans-Dihydronarciclasine. / Varró, Gábor; Hegedûs, L.; Simon, András; Balogh, Attila; Grün, A.; Leveles, Ibolya; Vértessy, B.; Kádas, István.

In: Journal of Natural Products, Vol. 80, No. 6, 23.06.2017, p. 1909-1917.

Research output: Contribution to journalArticle

Varró, Gábor ; Hegedûs, L. ; Simon, András ; Balogh, Attila ; Grün, A. ; Leveles, Ibolya ; Vértessy, B. ; Kádas, István. / The First Enantioselective Total Synthesis of (-)-Trans-Dihydronarciclasine. In: Journal of Natural Products. 2017 ; Vol. 80, No. 6. pp. 1909-1917.
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