Enantioselective synthesis of Anomala osakana pheromone and Janus integer pheromone: a flexible approach to chiral gamma-butyrolactones.
The enantioselective synthesis of Anomala osakana pheromone and Janus integer pheromone has been achieved without using any protecting groups. The synthesis involved using an asymmetric alkynylation to obtain gamma-hydroxy-alpha,beta-acetylenic esters with high ee (84%) and yields ( approximately 80%), followed by selective hydrogenation and lactonization in high overall yields (87% and 89%).
Lin
Li
L
State Key Laboratory of Applied Organic Chemistry and Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou, 730000, China.
Zhao
Qiangyang
Q
Li
A-Ni
AN
Ren
Fengbo
F
Yang
Fanzhi
F
Wang
Rui
R
D015107:4-Butyrolactone / Q000737:chemistry*; D000818:Animals; D001517:Coleoptera / Q000737:chemistry*; D005260:Female; D006927:Hymenoptera / Q000737:chemistry*; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D010675:Pheromones; D015107:4-Butyrolactone