title: Asymmetric total synthesis of alkaloids 223A and 6-epi-223A.
abstract: Concise and asymmetric total synthesis of the title compounds are described. The key ring system was constructed using an intramolecular Schmidt reaction on a norbornenone derivative, which was subsequently subjected to ring-opening metathesis followed by reduction. An unusual isomerization of the C-6 ethyl group afforded the desired stereochemistry of the natural product. The synthesis is readily adaptable to analogue production.
authors.affiliation: Department of Medicinal Chemistry, 1251 Wescoe Hall Drive, Malott Hall, Room 4070, University of Kansas, Lawrence, Kansas 66045-7582, USA.
authors.forename: Partha
authors.initials: P
authors.lastname: Ghosh
authors.forename: Weston R
authors.initials: WR
authors.lastname: Judd
authors.forename: Timothy
authors.initials: T
authors.lastname: Ribelin
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Aubé
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D054836:Indolizidines; D007769:Lactams