title: Stereoselective synthesis of 3-alkyl-2-aryltetrahydrofuran-4-ols: total synthesis of (+/-)-paulownin.
abstract: A formal [3 + 2]-cycloaddition involving the Lewis acid mediated reaction of alpha-silyloxy aldehydes and styrenes to afford 3-alkyl-2-aryltetrahydrofuran-4-ols has been developed. This methodology was applied to the total synthesis of the naturally occurring furofuran lignan (+/-)-paulownin.
authors.affiliation: Department of Chemistry, Wright State University, Dayton, Ohio 45435, and Department of Chemistry, University of California, Riverside, California 92521, USA. steven.angle@wright.edu
authors.forename: Steven R
authors.initials: SR
authors.lastname: Angle
authors.forename: Inchang
authors.initials: I
authors.lastname: Choi
authors.forename: Fook S
authors.initials: FS
authors.lastname: Tham
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry
chemical_list: D000447:Aldehydes; D001952:Bridged-Ring Compounds; D005663:Furans; D017705:Lignans; D013343:Styrenes; C008773:paulownin