title: A convergent approach to the dioxaadamantane core of (±)-tetrodotoxin.
abstract: A fully stereocontrolled 1,3-diol orthoesterification and a water-promoted intramolecular Henry addition, combined with the previously reported formal (3 + 3) annulation of α-nitro-α,β-enals and 2,2-dimethyl-1,3-dioxan-5-one, provided for a short convergent pathway to the dioxaadamantane core of (±)-tetrodotoxin.
authors.affiliation: Departments of Organic Chemistry and Physical Chemistry, University of Santiago de Compostela , Campus Vida s/n, 15782 Santiago de Compostela, A Coruña, Spain.
authors.forename: Hugo
authors.initials: H
authors.lastname: Lago-Santomé
authors.forename: Rubén
authors.initials: R
authors.lastname: Meana-Pañeda
authors.forename: Ricardo
authors.initials: R
authors.lastname: Alonso
mesh_terms: D000218:Adamantane / Q000138:chemical synthesis* / Q000737:chemistry*; D004146:Dioxanes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013779:Tetrodotoxin / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C519900:2,2-dimethyl-1,3-dioxan-5-one; D004146:Dioxanes; D013779:Tetrodotoxin; C025223:1,4-dioxane; D000218:Adamantane