Collect. Czech. Chem. Commun. 2002, 67, 83-90

The First Synthesis of Geranyllinalool Enantiomers

Aleš Svatoš*, Klára Urbanová and Irena Valterová

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic


(3R)-(-)-Geranyllinalool and its (3S)-(+)-isomer were synthesized in 7 steps starting from both enantiomers of citramalic acid and geranyl bromide. The synthetic sequence established the absolute configurations of naturally occurring geranyllinalools for the first time.

Keywords: Terpenoids; Diterpenes; Alcohols; Absolute configuration; Marking pheromones; Bumblebees; Cuprates; Cross-coupling reactions; Carbometallation.

References: 35 live references.