Synthesis of Sex Pheromone Components of Frankliniella intonsa and Casuarina Moth

• Main Authors: Chen, Po-Chih, 陳柏志
• Other Authors: Chen, Ching-Yuh
• Format: Others
• Language: zh-TW
• Online Access: http://ndltd.ncl.edu.tw/handle/18423223329804395853

碩士 === 國立嘉義大學 === 應用化學系研究所 === 104 === The major sex pheromone components of Frankliniella intonsa are nryl(S)-2-methylbutanoeate 1 and (R)-lavandulyl acetate 2. The construction of a chiral center was achieved by introducing a chiral auxiliary 2-oxazolidinones 23. Sex pheromone components 1 and 2’ were synthesized in 6 steps with 27% overall yield and 6 steps overall 17% yield, respectively. The major sex pheromone component of Lymantria xylina is cis-7,8-epoxy-2-methyleicosame 47. We take advantage of cheap cis-butyn-1-ol as starting material and coupling with bromododecane ather than hydrogenation and bromination. After followed by SN2 reaction with Grignard reagents, finally using mCPBA with expoxidation. Sex pheromone component 47 was synthesized in 7 steps overall 40% yield.