title: Enantioselective synthesis of Anomala osakana pheromone and Janus integer pheromone: a flexible approach to chiral gamma-butyrolactones.
abstract: 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%).
authors.affiliation: State Key Laboratory of Applied Organic Chemistry and Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Li
authors.initials: L
authors.lastname: Lin
authors.forename: Qiangyang
authors.initials: Q
authors.lastname: Zhao
authors.forename: A-Ni
authors.initials: AN
authors.lastname: Li
authors.forename: Fengbo
authors.initials: F
authors.lastname: Ren
authors.forename: Fanzhi
authors.initials: F
authors.lastname: Yang
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
mesh_terms: 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
chemical_list: D010675:Pheromones; D015107:4-Butyrolactone