4.8 Article

Total Synthesis of Selaginpulvilin C and D Relying on in Situ Formation of Arynes and Their Hydrogenation

Journal

ORGANIC LETTERS
Volume 18, Issue 23, Pages 6105-6107

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b03241

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Funding

  1. NSF [CHE-1361620]
  2. TACOMA Technology
  3. Direct For Mathematical & Physical Scien
  4. Division Of Chemistry [1361620] Funding Source: National Science Foundation

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The total syntheses of selaginpulvilins C and D is described. The key strategy for the construction of the core fluorene moiety involves in situ formation of an aryne intermediate followed by its formal hydrogenation. The precursor tetraynes that undergo aromatization via hexadehydro Diels Alder reaction were prepared from readily available building blocks through typical alkyne-coupling reactions.

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