Synthesis of 2-Geranyl- And 2-Farnesyl-Substituted Geranylgeraniols and Their Phosphates

Article abstract of DOI:10.1246/bcsj.69.2071

Allylation of the lithiated cyclohexylimine of (2E,6E, 10E)-geranylgeranial with (2E)-geranyl bromide followed by acid-catalyzed hydrolysis gave (2E)-α-, (2Z)-α-, and γ-geranyl-substituted geranylgeranials. Farnesyl-substituted geranylgeranials were also prepared. (2Z)-α-Geranyl- and (2Z)- α-farnesyl-substituted geranylgeranials were photoisomerized to the corresponding (2E)-isomers, respectively. The branched polyprenyl alcohols, obtained by the reduction of these aldehydes, were transformed to geranyl- and farnesyl-substituted geranylgeranyl phosphates.