title: Total synthesis of buergerinin F via effective construction of the asymmetric quaternary carbons using an enantioselective aldol reaction.
abstract: An efficient method for the synthesis of (+)-buergerinin F is established via the enantioselective aldol reaction of a tetra-substituted ketene silyl acetal with crotonaldehyde, followed by intramolecular Wacker-type ketalization.
authors.affiliation: Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. shiina@ch.kagu.tus.ac.jp
authors.forename: Isamu
authors.initials: I
authors.lastname: Shiina
authors.forename: Yo-ichi
authors.initials: Y
authors.lastname: Kawakita
authors.forename: Ryoutarou
authors.initials: R
authors.lastname: Ibuka
authors.forename: Kazutoshi
authors.initials: K
authors.lastname: Yokoyama
authors.forename: Yu-suke
authors.initials: YS
authors.lastname: Yamai
mesh_terms: D000080:Acetals / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D000447:Aldehydes; D005030:Ethylenes; D006575:Heterocyclic Compounds, 3-Ring; D007659:Ketones; D012821:Silanes; C479621:buergerinin F; D002244:Carbon; C116609:3-hydroxybutanal; C008223:ketene