Total synthesis of (+)-aureol

Org Lett. 2012 Sep 21;14(18):4710-3. doi: 10.1021/ol301715u. Epub 2012 Sep 4.

Abstract

A total synthesis of the marine sponge meroterpenoid (+)-aureol has been achieved in 12 steps (6% overall yield) from (+)-sclareolide. Key steps of the synthesis include a biosynthetically inspired sequence of 1,2-hydride and methyl shifts, and a biomimetic cycloetherification reaction.

MeSH terms

  • Animals
  • Diterpenes / chemistry*
  • Marine Biology
  • Molecular Structure
  • Porifera / chemistry
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Stereoisomerism

Substances

  • Diterpenes
  • Sesquiterpenes
  • aureol
  • sclareolide