title: A novel and highly stereoselective approach to aza-spirocycles. A short total synthesis of 2-epi-(+/-)-perhydrohistrionicotoxin and an unprecedented decarboxylation of 2-pyrones.
abstract: [reaction: see text] A novel and highly stereoselective synthesis of aza-spirocycles is described. An application of this methodology is illustrated as a short and concise total synthesis of 2-epi-(+/-)-perhydrohistrionicotoxin with high diastereomeric control at the aza-spirocenter. An unprecedented decarboxylation of the 2-pyrone ring is observed in this total synthesis effort.
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: McLaughlin
authors.forename: Richard P
authors.initials: RP
authors.lastname: Hsung
authors.forename: Kevin P
authors.initials: KP
authors.lastname: Cole
authors.forename: Juliet M
authors.initials: JM
authors.lastname: Hahn
authors.forename: Jiashi
authors.initials: J
authors.lastname: Wang
mesh_terms: D000664:Amphibian Venoms / Q000138:chemical synthesis*; D001372:Aza Compounds / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000664:Amphibian Venoms; D001372:Aza Compounds; D002264:Carboxylic Acids; D011753:Pyrones; C004792:perhydrohistrionicotoxin