Synthesis of natural products containing spiroketals via intramolecular hydrogen abstraction

Org Biomol Chem. 2010 Jan 7;8(1):29-38. doi: 10.1039/b916041h. Epub 2009 Oct 7.

Abstract

Although known for over a quarter of a century, the oxidative radical cyclisation route to spiroketals has found limited use in natural product synthesis in comparison to classical approaches. Its successful application in this field of research forms the subject of this perspective.

MeSH terms

  • Anthelmintics / chemical synthesis
  • Anthelmintics / chemistry
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Benzofurans / chemical synthesis
  • Benzofurans / chemistry
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Bridged-Ring Compounds / chemical synthesis
  • Bridged-Ring Compounds / chemistry
  • Ciguatoxins / chemical synthesis
  • Ciguatoxins / chemistry
  • Cyclization
  • Ethers / chemical synthesis
  • Ethers / chemistry
  • Ethers, Cyclic / chemical synthesis
  • Ethers, Cyclic / chemistry
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Hydrogen / chemistry*
  • Ivermectin / analogs & derivatives
  • Ivermectin / chemical synthesis
  • Ivermectin / chemistry
  • Molecular Structure
  • Oxazoles / chemical synthesis
  • Oxazoles / chemistry
  • Oxidation-Reduction
  • Phenazines / chemical synthesis
  • Phenazines / chemistry
  • Phosphoprotein Phosphatases / chemical synthesis
  • Phosphoprotein Phosphatases / chemistry
  • Pyrans / chemical synthesis
  • Pyrans / chemistry
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry

Substances

  • 5-hydroxy-7-methoxy-3-(5-(2-methyl-1,6-dioxaspiro(4,5)dec-7-yl)pentyl)-2-benzofuran-1(3H)-one
  • Anthelmintics
  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Benzofurans
  • Biological Products
  • Bridged-Ring Compounds
  • CP44,161
  • Ethers
  • Ethers, Cyclic
  • Furans
  • Oxazoles
  • Phenazines
  • Pyrans
  • Spiro Compounds
  • bistramide C
  • spiroketal
  • spirolide B
  • spirolide D
  • Ciguatoxins
  • salinomycin
  • Ivermectin
  • avermectin
  • calyculin A
  • Hydrogen
  • narasin
  • Phosphoprotein Phosphatases