CHIRAL BUILDING-BLOCKS BASED ON TECHNICAL GRADE BETA-CITRONELLENE

(+)-β-Citronellene, the main component of the technical grade pyrolysate of (+)-cis-pinane, can be chemoselectively processed to certain C-10 derivatives in the presence of isomeric C10 olefins. These derivatives are converted into mono- and bifunctional chiral building blocks suitable for the incorporation of ~MeCH~ fragments with or -configuration into aliphatic chains. Although their optical purity may be as low as 50%, that of the end products can be upgraded by inclusion of an optical resolution step in the synthetic sequence. © 1990 De Gruyter