title: Intramolecular carbolithiation as a route to a sterically congested cyclopentene: synthesis of the longtailed mealybug pheromone.
abstract: A concise preparation of the pheromone secreted by the female longtailed mealybug [viz., 2-(1,5,5-trimethylcyclopent-2-en-1-yl)ethyl acetate] (1) is described. The key step in the synthesis of 1 involves 5-exo-trig ring closure of the vinyllithium derived from (Z)-1-iodo-4,4,5-trimethyl-1,5-hexadiene by lithium-iodine exchange.
authors.affiliation: Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, USA. william.bailey@uconn.edu
authors.forename: William F
authors.initials: WF
authors.lastname: Bailey
authors.forename: Johanna M
authors.initials: JM
authors.lastname: Bakonyi
mesh_terms: D000085:Acetates / Q000138:chemical synthesis* / Q000737:chemistry; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C544051:2-(1,5,5-trimethylcyclopent-2-en-1-yl)ethyl acetate; D000085:Acetates; D003517:Cyclopentanes; D009942:Organometallic Compounds; D008094:Lithium