Total Synthesis of the Natural Product (+)-trans-Dihydronarciclasine via an Asymmetric Organocatalytic [3+3]-Cycloaddition and discovery of its potent anti-Zika Virus (ZIKV) Activity

Omkar Revu, Carlos Zepeda-Velázquez, Alex J. Nielsen, James McNulty, Robert H Yolken, Lorraine V Brando

Research output: Contribution to journalArticle

Abstract

An asymmetric total synthesis of the natural product (+)-trans-dihydronarciclasine has been achieved from α-azidoacetone and cinnamaldehyde precursors via a stepwise asymmetric [3+3]-organocatalytic cascade. The anti-Zika virus activity of this compound is also reported for the first time.

Original languageEnglish (US)
Pages (from-to)5895-5899
Number of pages5
JournalChemistrySelect
Volume1
Issue number18
DOIs
StatePublished - Jan 1 2016

Fingerprint

Cycloaddition
Biological Products
Viruses
dihydronarciclasine
cinnamic aldehyde

Keywords

  • alkaloids
  • aminocyclitols
  • antiviral
  • asymmetric synthesis
  • organocatalysis
  • total synthesis
  • Zika

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Total Synthesis of the Natural Product (+)-trans-Dihydronarciclasine via an Asymmetric Organocatalytic [3+3]-Cycloaddition and discovery of its potent anti-Zika Virus (ZIKV) Activity. / Revu, Omkar; Zepeda-Velázquez, Carlos; Nielsen, Alex J.; McNulty, James; Yolken, Robert H; Brando, Lorraine V.

In: ChemistrySelect, Vol. 1, No. 18, 01.01.2016, p. 5895-5899.

Research output: Contribution to journalArticle

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