4.8 Article

Palladium(II)-Catalyzed Cyclization of Unsaturated Hydroperoxides for the Synthesis of 1,2-Dioxanes

Journal

ORGANIC LETTERS
Volume 11, Issue 15, Pages 3290-3293

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol901046z

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Funding

  1. National Institute of General Medical Sciences of the National Institutes of Health [GM-61066]
  2. National Science Foundation [CHE-0315572]
  3. Eli Lilly
  4. National Institute of General Medical Sciences for a postdoctoral fellowship [GM-085910]
  5. Direct For Mathematical & Physical Scien [0848121] Funding Source: National Science Foundation
  6. Division Of Chemistry [0848121] Funding Source: National Science Foundation

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The cyclization of gamma,delta-unsaturated tertiary hydroperoxides in the presence of a palladium(II) catalyst afforded 1,2-dioxanes resembling biologically active natural products. A variety of substrates were screened, and synthetic manipulations were accomplished to construct compounds with structural similarity to antimalarial targets.

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