title: The new method for introduction of an allyl group into the angular position of 2-(TBS-oxymethyl)-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one and its application to chiral Wieland-Miescher type compound synthesis.
abstract: The stereoselective introduction of an allyl group into the angular position of 2-(TBS-oxymethyl)-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one was accomplished using Birch reduction and an enolate trapping reaction. It was determined that the allyl group was introduced via an unexpected conformation-flipped from the initially formed one. Two diastereomeric Wieland-Miescher type compounds, having the allyl group at the angular position, were synthesized as optically pure forms.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai, Japan. hiroya@mail.tains.tohoku.ac.jp
authors.forename: Kou
authors.initials: K
authors.lastname: Hiroya
authors.forename: Taisuke
authors.initials: T
authors.lastname: Takahashi
authors.forename: Katsunori
authors.initials: K
authors.lastname: Shimomae
authors.forename: Takao
authors.initials: T
authors.lastname: Sakamoto
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D007202:Indicators and Reagents; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis*
chemical_list: D001578:Benzopyrans; D007202:Indicators and Reagents; D014315:Triterpenes