5 光学活性昆虫フェロモン類の合成

概要

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(S)-(-)-Frontalin (4') was synthesized and shown to be attractive to western pine beetles, while (R)-(+)-enantiomer (4) was inactive. This proved the chiral nature of the pheromone receptor of the insect. Two pheromones, sulcatol (8) and ipsenol (14), were synthesized from amino acids in optically active forms. Since these pheromones are derivatives of monoterpenes, amino acids can be regarded as usedful starting materials for the synthesis of chiral terpenes. Natural (-)-ipsenol (14) was shown to possess S-configration by its derivation from (S)-(+)-leucine (16). A noteworthy feature of the ipsenol synthesis was the use of an optically active α-methylene-γ-lactine (22) as the key intermediate.
天然有機化合物討論会の論文
1975-10-01