Stereoselective synthesis of 3-alkyl-2-aryltetrahydrofuran-4-ols: total synthesis of (+/-)-paulownin.
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.
Angle
Steven R
SR
Department of Chemistry, Wright State University, Dayton, Ohio 45435, and Department of Chemistry, University of California, Riverside, California 92521, USA. steven.angle@wright.edu
Choi
Inchang
I
Tham
Fook S
FS
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
D000447:Aldehydes; D001952:Bridged-Ring Compounds; D005663:Furans; D017705:Lignans; D013343:Styrenes; C008773:paulownin