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A versatile, non-biomimetic route to the preussomerins: syntheses of (+/-)-preussomerins F, K and L

Research output: Contribution to journalArticle

Author(s)

  • E Quesada
  • M Stockley
  • J P Ragot
  • M E Prime
  • A C Whitwood
  • R J K Taylor

Department/unit(s)

Publication details

JournalOrganic and Biomolecular Chemistry
DatePublished - 2004
Issue number17
Volume2
Number of pages13
Pages (from-to)2483-2495
Original languageEnglish

Abstract

The first total syntheses of the title fungal metabolites preussomerins F, K and L are described and their structures confirmed thereby. The syntheses were achieved following a versatile, unified, non-biomimetic approach, which is easily extendable to prepare other known and novel members of this family. Key steps include the functionalisation of a 2-arylacetal anion, tandem one-pot Friedel-Crafts cyclisation-deprotection, regioselective substrate-directable hydrogenation and reductive-opening of epoxides.

    Research areas

  • BIOLOGICALLY-ACTIVE METABOLITES, ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS, CRYSTAL-STRUCTURE ANALYSIS, FUNGUS PREUSSIA-ISOMERA, SILYL ENOL ETHERS, STRUCTURE ELUCIDATION, FARNESYLTRANSFERASE INHIBITORS, ANTIFUNGAL METABOLITES, ABSOLUTE-CONFIGURATION, CONIOTHYRIUM-PALMARUM

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