Synthesis of (3aR,8S,8bS,2'R)-(+)-sorgolactone and its stereoisomers, the germination stimulant from sorghum bicolor

Article abstract of DOI:10.1016/S0040-4039(97)10078-8

Methyl (S)-citronellate (2) was converted to (3aR,8S,8bS,2'R)-(+)- sorgolactone (1a) by employing the radical cyclization of 6 to 7 as the key- step. Three other stereoisomers (1b, 1c and 1d) of sorgolactone were also prepared. The CD spectrum of la was in accord with that reported for the natural product.