Synthesis of the C4-epi-lomaiviticin B Core Reveals Subtle Stereoelectronic Effects

Org Lett. 2013 May 17;15(10):2390-3. doi: 10.1021/ol400832r. Epub 2013 May 9.

Abstract

An efficient synthesis of the C4-epi-lomaiviticin B core is reported. The synthesis features a diastereoselective anionic formal furan Diels-Alder reaction and a stereoselective oxidative enolate dimerization. During the investigation, subtle yet critical stereoelectronic effects imparted by the C4-stereocenter were observed.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Cycloaddition Reaction
  • Fluorenes / chemical synthesis*
  • Fluorenes / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Fluorenes
  • lomaiviticin B