Application of the Rodriguez-Pattenden photo-ring contraction: total synthesis and configurational reassignment of 11-gorgiacerol and 11-epigorgiacerol

Org Lett. 2012 Jun 1;14(11):2834-7. doi: 10.1021/ol301068h. Epub 2012 May 16.

Abstract

A stereospecific photochemical ring contraction was used as the key step in the first total synthesis of the marine pseudopteranyl diterpene 11-gorgiacerol and its 11-epimer. The synthesis allowed the correction of the configurations that had been misassigned in the literature. In addition, some novel pseudopteranyl derivatives have been made.

MeSH terms

  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Marine Biology
  • Molecular Structure
  • Photochemical Processes
  • Stereoisomerism

Substances

  • 11-gorgiacerol
  • Diterpenes