Synthesis of 1,2-oxygenated 6-arylfurofuran lignan: stereoselective synthesis of (1S,2S,5R,6S)-1-hydroxysamin.
(1S,2S,5R,6S)-6-(3,4-Methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octan-1,2-diol ((+)-1-hydroxysamin 1) was synthesized, starting from olefin 8. Stereoselective alpha-hydroxylation was achieved after converting 8 to aldehyde 13. Resulting unstable alpha-hydroxy aldehyde 14 was then transformed to (+)-1-hydroxysamin (1). This is a new efficient synthetic route to 1,2-oxygenated 6-arylfurofuran lignans.
Yamauchi
Satoshi
S
College of Agriculture, Ehime University, Matsuyama, Japan. syamauch@agr.ehime-u.ac.jp
Bando
Satoshi
S
Kinoshita
Yoshiro
Y
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D004149:Dioxoles / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D006900:Hydroxylation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
C472487:1-hydroxysamin; D000447:Aldehydes; D000475:Alkenes; D004149:Dioxoles; D005663:Furans; D007202:Indicators and Reagents