title: Total synthesis of a cuticular hydrocarbon from the cane beetle Antitrogus parvulus: confirmation of the relative stereochemistry.
abstract: The stereoselective reaction of an allyl bromide with an aldehyde mediated by a low valency bismuth species was the key reaction in stereoselective syntheses of (4S,6R,8R,10S,16S)- and (4S,6R,8R,10S,16R)-4,6,8,10,16-pentamethyldocosanes. (13)C NMR data for these compounds confirmed that the cuticular hydrocarbon isolated from the cane beetle Antitrogus parvulus was the (4S,6R,8R,10S,16S)-stereoisomer.
authors.affiliation: Universiti Teknologi Malaysia, 81310 Skudai, Johor, Malaysia.
authors.forename: Norazah B
authors.initials: NB
authors.lastname: Basar
authors.forename: Hao
authors.initials: H
authors.lastname: Liu
authors.forename: Devendra
authors.initials: D
authors.lastname: Negi
authors.forename: Hasnah M
authors.initials: HM
authors.lastname: Sirat
authors.forename: Gareth A
authors.initials: GA
authors.lastname: Morris
authors.forename: Eric J
authors.initials: EJ
authors.lastname: Thomas
mesh_terms: D000818:Animals; D001517:Coleoptera / Q000033:anatomy & histology / Q000737:chemistry*; D006838:Hydrocarbons / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006838:Hydrocarbons