Synthesis of grandisol, the sexual attracting insect pheromone

Arch Pharm Res. 2011 Sep;34(9):1399-402. doi: 10.1007/s12272-011-0900-y.

Abstract

In this issue, Suh's group reported a new formal total synthesis of (±)-grandisol featuring a palladium-catalyzed 4-exo-trig cyclization. Grandisol's interesting cyclobutane structure has been a popular test model for various cyclization methods over the years. This report summarizes Suh's formal synthesis of grandisol along with a concise review of the four-membered ring cyclization strategies employed in the synthesis of grandisol.

MeSH terms

  • Animals
  • Catalysis
  • Cyclization
  • Molecular Structure
  • Palladium / chemistry
  • Sex Attractants / chemical synthesis*
  • Sex Attractants / chemistry
  • Sex Attractants / pharmacology
  • Stereoisomerism
  • Terpenes / chemical synthesis*
  • Terpenes / chemistry
  • Terpenes / pharmacology
  • Weevils*

Substances

  • Sex Attractants
  • Terpenes
  • Palladium
  • grandisol