Synthesis of (±)-bicolorin, the aggregation pheromone of beech bark beetle Taphrorychus bicolor

Recent advances in the synthesis of insect pheromones: an overview from 2013 to 2022

“…Fig. 10 summarizes the acetals as pheromones of Dendroctonus ponderosae (Col., Curculionidae): 210 , 197 D. brevicomis (Col., Curculionidae): endo - and exo - 211 , 197–200 D. frontalis (Col., Curculionidae): 212 , 201 Taphrorychus bicolor (Col., Curculionidae): 213 , 202 Cantao parentum (Hem., Scutelleridae): 214 , 203 Pityogenes chalcographus (Col., Curculionidae): 215 , 204 and Dacus oleae (Dip., Tephritidae): 216 . 205,206 In all cases, the acetal function was obtained via the corresponding dihydroxyketones.…”

“…192 Agrilus planipennis (Col., Buprestidae): 205, 193,194 Oryzaephilus surinamensis (Col., Silvanidae): 206 and 207, 195 Cryptoletes pusillus (Col., Staphylinidae): 208, 47 Oryzaephilus surinamensis (Col., Silvanidae): 209. 196 The lactone function was obtained mainly by intramolecular esterication of a hydroxy acid, e.g., using Yamaguchi lactonization conditions (202) or BOP-Cl lactonization (204), and by ring-closing metathesis reactions (200,203,(206)(207)(208)(209). An enantioselective synthesis of the pheromones of Popillia japonica and Anomala osakana (R)-and (S)-japonilure (197), respectively, was performed by .…”

“…178 Hötling et al or NADP + , GDH, glucose, 24 h (for 3R,4R-65: ee = 99%, de = 99%; for 3S,4R-65: ee = 92%, de = 99%; for 3R, 4S-166: ee = 99%, de = 92%; for 3S,4S-166: ee = 99%, de = 94%). 202 Cantao parentum (Hem., Scutelleridae): 214, 203 Pityogenes chalcographus (Col., Curculionidae): 215, 204 and Dacus oleae (Dip., Tephritidae): 216. 205,206 In all cases, the acetal function was obtained via the corresponding dihydroxyketones.…”