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Generation of Dithianyl and Dioxolanyl Radicals Using Photoredox Catalysis: Application in the Total Synthesis of the Danshenspiroketallactones via Radical Relay Chemistry.

Yifan DengMinh D NguyenYike ZouKendall N HoukAmos B Smith Iii
Published in: Organic letters (2019)
Visible-light-induced generation of dithianyl and dioxolanyl radicals via selective hydrogen atom transfer (HAT) has been achieved. This radical relay tactic enables remote C(sp3)-H functionalization to permit rapid access to polyol and spiroketal segments, and in turn has been exploited as a key synthetic construct in the total synthesis of the danshenspiroketallactones. The conformational stability of the danshenspiroketallactones has also been defined via experiments and DFT calculations.
Keyphrases
  • molecular dynamics
  • density functional theory
  • visible light
  • molecular dynamics simulations
  • single molecule
  • fluorescent probe
  • electron transfer