Synthesis of optically active olivil type of lignan from L-arabinose using threo-selective aldol condensation as a key reaction.
The threo-selective aldol condensation of (3R, 4S)-3-hydroxy-5-trityloxy-4-pentanolide, which was prepared from L-arabinose, with piperonal was applied to the stereoselective synthesis of the olivil type of lignan, (2R, 3R, 4R)-4-benzyl-4-hydroxy-3-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran.
Yamauchi
S
S
College of Agriculture, Ehime University, Ehime, Japan. syamauch@agr.ehime-u.ac.jp
Kinoshita
Y
Y
D000447:Aldehydes / Q000737:chemistry; D001089:Arabinose / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry; D052117:Benzodioxoles; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D009904:Optical Rotation; D013237:Stereoisomerism
D000447:Aldehydes; D001547:Benzaldehydes; D052117:Benzodioxoles; D017705:Lignans; C116609:3-hydroxybutanal; D001089:Arabinose; C005454:piperonal