Concise synthesis of rodgersinol and determination of the C-10 absolute configuration

J Org Chem. 2007 Jan 19;72(2):666-8. doi: 10.1021/jo061980u.

Abstract

Rodgersinol was synthesized via seven linear steps in 31% overall yield, and the absolute configuration of the C-10 stereogenic center was elucidated. The key feature of the synthesis involves the efficient Cu(II)-mediated coupling of two aromatic moieties for the diaryl ether intermediate and the enantioselective construction of the hydroxypropyl substituent by a regio- and stereoselective methyl addition to the chiral aryloxiranes in an inversion manner.

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkenes / chemistry
  • Molecular Structure
  • Phenols / chemical synthesis*
  • Phenols / chemistry
  • Saxifragaceae / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Phenols
  • rodgersinol