A new route to methyl (R,E)-(-)-tetradeca-2,4,5-trienoate (pheromone of Acanthoscelides obtectus) utilizing a palladium-catalyzed asymmetric allene formation reaction.
[reaction: see text] A formal total synthesis of the sex attractant of male dried bean beetle, methyl (R,E)-(-)-tetradeca-2,4,5-trienoate, was achieved by a new efficient route utilizing the Pd-catalyzed asymmetric allene synthesis reaction. It was found that the atropisomeric biaryl bisphosphine (R)-segphos showed better enantioselectivity than (R)-binap in the Pd-catalyzed reaction for preparing alkyl-substituted axially chiral allenes.
Catalysis Research Center and Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-ku, Sapporo 001-0021, Japan. ogasawar@cat.hokudai.ac.jp
Masamichi
M
Ogasawara
Takashi
T
Nagano
Tamio
T
Hayashi
D000466:Alkadienes / Q000737:chemistry*; D000818:Animals; D002384:Catalysis; D001517:Coleoptera; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010675:Pheromones / Q000138:chemical synthesis; D010720:Phosphines / Q000737:chemistry; D013237:Stereoisomerism
D000466:Alkadienes; D010675:Pheromones; D010720:Phosphines; D010165:Palladium