title: Synthesis of (±)-acetylnorloline via stereoselective tethered aminohydroxylation.
abstract: Loline alkaloids exhibit a strained ether-bridged pyrrolizidine skeleton and possess insecticidal and insect antifeedant properties. The synthesis of acetylnorloline, a prototypical member of the alkaloid family, is described. Central to the route is a stereoselective tethered aminohydroxylation (TA) of a homoallylic carbamate. Allylic (A1,3) strain is exploited to enforce diastereofacial selectivity during the aminohydroxylation.
authors.affiliation: Department of Chemistry, The College of William & Mary, Williamsburg, Virginia 23187, USA.
authors.forename: M Todd
authors.initials: MT
authors.lastname: Hovey
authors.forename: Emily J
authors.initials: EJ
authors.lastname: Eklund
authors.forename: Robert D
authors.initials: RD
authors.lastname: Pike
authors.forename: Anshul A
authors.initials: AA
authors.lastname: Mainkar
authors.forename: Jonathan R
authors.initials: JR
authors.lastname: Scheerer
mesh_terms: D000470:Alkaloids / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D055329:Epichloe / Q000737:chemistry; D006900:Hydroxylation; D008129:Lolium / Q000382:microbiology; D015394:Molecular Structure; D055328:Neotyphodium / Q000737:chemistry; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000588:Amines; D011763:Pyrrolizidine Alkaloids; C557932:acetylnorloline; C059478:loline