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Cycloaddition of cyclohexa-2,4-dienones, ring-closing metathesis, and photochemical reactions: A common stereoselective approach to duprezianane, polyquinane and sterpurane frameworks

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DSpace at IIT Bombay
Keywords
  • 1St Total-Synthesis
  • Di-Pi-Methane
  • Fungus Stereum-Purpureum
  • Diels-Alder Reactions
  • Organic-Synthesis
  • Natural-Products
  • Chemoenzymatic Synthesis
  • Periodate Oxidation
  • Olefin-Metathesis
  • Linear Triquinane
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Abstract

A novel approach to three different types of carbocyclic frameworks belonging to dupreziananes, sterpuranes, and polyquinanes from simple aromatic precursors has been presented. Cycloaddition of appropriately appended cyclohexa-2,4-dienones with acyclic dienes gave bridged bicyclic octanes suitably disposed with olefinic chains, which upon ring-closing metathesis led to functionalized tricyclo[5.2.2.0(1,5)]undecanes related to dupreziananes. Photochemical sigmatropic 1,2- and 1,3-acyl shifts in tricyclo[5.2.2.0(1,5)] undecanes upon triplet and singlet excitation provided stereoselective routes to sterpurane and polyquinane frameworks.

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