Furanylidene Systems from a Tosylic Acid- Mediated, Tandem Desilylation-Cyclization Reaction of Silyl Ethers of Monoalkynylated Β -Keto Carbonyls

John Oxford, Rayaj Ahamed, Morgan Hudson-Davis, Brandi Womack, Laura Gessner, Kristina Deveaux, Ebonni Fisher, Karelle S. Aiken

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Single isomers of the furanylidene system 8 were synthesized in four steps. The synthesis begins with the dianion of β-keto carbonyls and culminates in a mild, tandem desilylationcyclization reaction using tosylic acid. Compounds synthesized in this study have the potential for further diversification at the alkyne, carbonyl and enol-ether moieties. Hence, the furanylidenes from this study are prospective building blocks for biologically active, furan-containing natural products and their analogs. 2011 ·

Original languageAmerican English
JournalHeterocyclic Communications
Volume17
DOIs
StatePublished - Jan 1 2011

Disciplines

  • Chemistry
  • Organic Chemistry

Keywords

  • Desilylation
  • Furanylidene
  • Silyl ether
  • Tosylic acid

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