Regioselective Pd-catalyzed synthesis and application of 3-methyl-5-bromo-2-pyrone toward keto-phomactin A

Org Lett. 2006 Jul 20;8(15):3343-5. doi: 10.1021/ol061231z.

Abstract

[Structure: see text] An efficient one-step synthetic protocol for 3-methyl-5-bromo-2-pyrone was developed using the C3-selective Pd-catalyzed coupling reaction of 3,5-dibromo-2-pyrone with Me3Al-dimethylaminoethanol complex. A subsequent seven-step reaction sequence provided a cyclohexenyl bromide, which served as the key intermediate for the synthesis of the keto analogue of phomactin A, in 31% overall yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aluminum / chemistry
  • Catalysis
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry
  • Palladium / chemistry*
  • Pyrones / chemistry*

Substances

  • 3-methyl-5-bromo-2-pyrone
  • Heterocyclic Compounds, 4 or More Rings
  • Organometallic Compounds
  • Pyrones
  • phomactin A
  • Palladium
  • Aluminum