Efficient synthesis of (+)-MK7607 and its C-1 epimer via the stereoselective transposition of a tertiary allylic alcohol

Org Lett. 2009 Jun 18;11(12):2583-6. doi: 10.1021/ol9008987.

Abstract

These studies provide an efficient and stereoselective synthetic route to (+)-MK7607 and its C-1 epimer from a common intermediate in high overall yields. The synthetic methodologies mainly rely on the stereospecific 1,3-allylic transposition of the hindered tertiary alcohol group through a palladium-catalyzed allylic rearrangement as well as a PBr(3)-mediated allylic-transposed bromination.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Galactose / chemistry*
  • Molecular Structure
  • Palladium / chemistry
  • Phenols / chemical synthesis*
  • Phenols / chemistry
  • Propanols / chemistry*
  • Stereoisomerism

Substances

  • MK7607
  • Phenols
  • Propanols
  • allyl alcohol
  • Palladium
  • Galactose