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.
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.
Hiroya
Kou
K
Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai, Japan. hiroya@mail.tains.tohoku.ac.jp
Takahashi
Taisuke
T
Shimomae
Katsunori
K
Sakamoto
Takao
T
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*
D001578:Benzopyrans; D007202:Indicators and Reagents; D014315:Triterpenes