title: Enantioselective total synthesis of (+)-amabiline.
abstract: The first total synthesis of (+)-amabiline, an unsaturated pyrrolizidine alkaloid from Cynoglossum amabile, is reported. This convergent, enantioselective synthesis proceeds in 15 steps (10-step longest linear sequence) in 6.2% overall yield and features novel methodology to construct the unsaturated pyrrolizidine or (-)-supinidine core.
authors.affiliation: Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37232, USA.
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Senter
authors.forename: Olugbeminiyi O
authors.initials: OO
authors.lastname: Fadeyi
authors.forename: Craig W
authors.initials: CW
authors.lastname: Lindsley
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D028082:Boraginaceae / Q000737:chemistry; D015394:Molecular Structure; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D047151:Amaryllidaceae Alkaloids; D011763:Pyrrolizidine Alkaloids; C542589:amabiline; C011549:supinidine