title: Integral stereocontrolled synthesis of a spiro-norlignan, sequosempervirin A: revision of absolute configuration.
abstract: A novel synthetic path to sequosempervirin A was established by employing a samarium diiodide promoted intramolecular Barbier-type reaction of the lactonic iodide, in which the key structural feature, a spiro[4.5]decane ring system, could be constructed by controlling the stereochemistry of the hydroxyl group at the 8-position. The absolute configuration of natural sequosempervirin A was revised to be 4S based on this synthesis.
authors.affiliation: Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan.
authors.forename: Yuji
authors.initials: Y
authors.lastname: Ito
authors.forename: Kazunori
authors.initials: K
authors.lastname: Takahashi
authors.forename: Hiromasa
authors.initials: H
authors.lastname: Nagase
authors.forename: Toshio
authors.initials: T
authors.lastname: Honda
mesh_terms: D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D013141:Spiro Compounds; C568024:sequosempervirin A