title: Reactive enols in synthesis 2. Synthesis of (+)-latifolic acid and (+)-latifoline.
abstract: We describe a short, enantioselective synthesis of the naturally occurring pyrrolizidine alkaloid (+)-latifoline (1) employing a tandem [3,3] sigmatropic rearrangement/[1,2] allyl shift as a key step in constructing (+)-latifolic acid (4).
authors.affiliation: Department of Chemistry, Yale University, Sterling Chemistry Laboratory, P.O. Box 208107, New Haven, Connecticut 06520-8107, USA.
authors.forename: I
authors.initials: I
authors.lastname: Drutu
authors.forename: E S
authors.initials: ES
authors.lastname: Krygowski
authors.forename: J L
authors.initials: JL
authors.lastname: Wood
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D028082:Boraginaceae / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D007783:Lactones; D011763:Pyrrolizidine Alkaloids; C459704:latifolic acid; C459703:latifoline