title: Enantioselective synthesis of protected nitrocyclohexitols with five stereocenters. Total synthesis of (+)-pancratistatin.
abstract: 2-Methoxymethylpyrrolidine best performed, among several other proline derivatives, to control the enantioselective [3+3] annulation of β-(hetero)aryl-α-nitro-α,β-enals with commercial 2,2-dimethyl-1,3-dioxan-5-one, a procedure that renders highly oxygenated nitrocyclohexanes endowed with five new stereocenters. Use of this reaction allowed the development of a total synthesis of the antitumoral natural product (+)-pancratistatin; it also converted our previous racemic route to tetrodotoxin into an enantioselective one.
authors.affiliation: Department of Organic Chemistry, University of Santiago de Compostela, Campus Vida sn, 15782 Santiago de Compostela, A Coruña, Spain.
authors.forename: Fernando
authors.initials: F
authors.lastname: Cagide-Fagín
authors.forename: Olaia
authors.initials: O
authors.lastname: Nieto-García
authors.forename: Hugo
authors.initials: H
authors.lastname: Lago-Santomé
authors.forename: Ricardo
authors.initials: R
authors.lastname: Alonso
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D007294:Inositol / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D047151:Amaryllidaceae Alkaloids; D007546:Isoquinolines; D007294:Inositol; C044997:pancratistatin