Stereoselective synthesis of tetrahydrofurans via formal [3+2]-cycloaddition of aldehydes and allylsilanes. Formal total synthesis of the muscarine alkaloids (-)-allomuscarine and (+)-epimuscarine.
The stereoselective synthesis of tetrahydrofurans was achieved by formal [3+2]-cycloaddition of allyl and crotylsilanes with alpha-triethylsilyloxy aldehydes. The scope of the reaction was examined by using different alpha-substituted aldehydes and different substituents on the silicon. Tamao oxidation of the products resulted in formation of diols that are easily functionalized allowing an entry to natural products synthesis. The formal total synthesis of the muscarine alkaloids (-)-allomuscarine and (+)-epimuscarine was achieved.
Angle
Steven R
SR
Department of Chemistry, University of California-Riverside, Riverside, California 92521-0403, USA.
El-Said
Nahla A
NA
D000447:Aldehydes / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D009116:Muscarine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D010084:Oxidation-Reduction; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000470:Alkaloids; D000498:Allyl Compounds; D005663:Furans; D012821:Silanes; C455960:allomuscarine; C455961:epimuscarine; C018674:tetrahydrofuran; D009116:Muscarine