Total Synthesis of (-)-Hymenosetin

J Org Chem. 2016 Jan 4;81(1):215-28. doi: 10.1021/acs.joc.5b02526. Epub 2015 Dec 16.

Abstract

The 3-decalinoyltetramic acid (-)-hymenosetin and its N-methyl analogue were prepared in 11 and 8 steps, respectively, from (+)-citronellal using an intramolecular Diels-Alder reaction as the key step. This method represents the first example for the synthesis of a 3-decalinoyltetramic acid with a free NH moiety. The stereochemistry of the title compound, an unnatural diastereomer, and of a decalin building block was studied in detail using circular dichroism spectroscopy in the IR and UV/VIS freqeuncy range. This allowed to determine the absolute configuration of the natural product and to plan the synthetic route.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Cycloaddition Reaction
  • Molecular Structure
  • Pyrrolidinones / chemical synthesis*
  • Pyrrolidinones / chemistry
  • Stereoisomerism

Substances

  • Biological Products
  • Pyrrolidinones
  • hymenosetin