Asymmetric synthesis of (R)-sulcatol
Davies SG., Smyth GD.
The insect pheromone (R)-sulcatol, 2-hydroxy-6-methylhept-5-ene, is synthesized via a stereoselective conjugate addition of (R)-lithium N,α-dimethylbenzylamide to tert-butyl (E,E)-hexa-2,4-dienoate, Grignard addition, and stereospecific Meisenheimer rearrangement. Hydrogenation of the olefin, dehydration of the tertiary alcohol and N-O bond cleavage complete the synthesis.