TY - JOUR
T1 - Efficient synthesis of beetle aggregation pheromone frontalin and its analogues
AU - Yang, Xiaobao
AU - Luo, Shengjun
AU - Hua, Chengwen
AU - Zhai, Hongbin
N1 - Funding Information:
We thank the following agencies for financial support: Chinese Academy of Sciences (‘Hundreds of Talent’ Program); Science & Technology Commission of Shanghai Municipality (‘Venus’ Program); National Natural Science Foundation of China (20102008).
PY - 2003/10/20
Y1 - 2003/10/20
N2 - (-)-Frontalin is an aggregation pheromone that has found application in selective exterminating of certain harmful insects. This paper discloses an expedite synthesis of (±)-frontalin from a symmetric molecule, 2,6-dimethyl-1,6-heptadiene, in 64% yield. The one-flask operation consists of double dihydroxylation, mono-cleavage, and acid-catalyzed intramolecular acetalation. Our unique strategy was also successfully applied to additional diene substrates such as 4a and 4b.
AB - (-)-Frontalin is an aggregation pheromone that has found application in selective exterminating of certain harmful insects. This paper discloses an expedite synthesis of (±)-frontalin from a symmetric molecule, 2,6-dimethyl-1,6-heptadiene, in 64% yield. The one-flask operation consists of double dihydroxylation, mono-cleavage, and acid-catalyzed intramolecular acetalation. Our unique strategy was also successfully applied to additional diene substrates such as 4a and 4b.
KW - Aggregation pheromone
KW - Double dihydroxylation
KW - Frontalin
KW - Intramolecular acetalation
KW - Synthesis
UR - http://www.scopus.com/inward/record.url?scp=0141594840&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2003.09.029
DO - 10.1016/j.tet.2003.09.029
M3 - Article
AN - SCOPUS:0141594840
SN - 0040-4020
VL - 59
SP - 8551
EP - 8553
JO - Tetrahedron
JF - Tetrahedron
IS - 43
ER -