Synthesis of (+)-Luzofuran and (−)-Ancistrofuran

The first synthesis of the furan-containing snyderane, (+)-luzofuran, is reported. The key step in this approach was an electrophilic brominative cyclization, which was accomplished using a nucleophilic N-heterocycle-flanked phosphoramidite catalyst in combination with the common laboratory reagent N-bromosuccinimide.

• Publication year

  2014

• Venue

  Journal of Organic Chemistry

• Publication date

  2014-01-17

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/jo402790xPMID 24437567PMCID 3985840
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Chirality

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  2010cited by this paper
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  1991cited by this paper
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  1985cited by this paper
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  1978cited by this paper
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  1976cited by this paper
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  1971cited by this paper
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  1957cited by this paper
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  1955cited by this paper
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  1955cited by this paper

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