Synthesis of (+)-(1S,2S,5R,6S)-1-Hydroxysamin froml-(+)-Arabinose

Synthesis of 1,2-Oxygenated 6-arylfurofuran Lignan: Stereoselective Synthesis of (1S,2S,5R,6S)-1-hydroxysamin

“…Resulting unstable a-hydroxyaldehyde 14 was therefore immediately treated with tetrabutylammonium ‰uoride to cleave the silyl ether, giving (1S,2S,5R,6S)-1-hydroxysamin 1 as a single isomer in 78z yield: [a]D 20 +74.5, c 0.51 in CHCl3; lit. 3) [a]D 20 +74.8, c 0.21 in CHCl3. The NMR data agreed with previously described data.…”

“…The NMR data agreed with previously described data. 3) This new stereoselective synthetic method for (1S,2S,5R,S )-1-hydroxysamin (1) involved 14 steps from (S )-4-benzyl-2-oxazolidinone and 4-pentenoic acid to provide 12z overall yield. This is a more e‹cient synthetic method than that previously described (25 steps, 0.3z overall yield).…”

“…The synthetic study of this furofuran lignan is important for further research into its biological activity, and many synthetic routes has been developed. 2) Our synthetic study has been focused on the 1,2-oxygenated 6-arylfurofuran lignans, 3) 1 and 2, because only a few synthetic route to this type of lignan have been reported. 4),5) This study is expected to contribute to biological research into the structure-activity relationship of furofuran lignan and to discover new biological activities of 1,2-oxygenated 6-arylfurofuran lignan.…”

“…This present report describes the stereoselective synthesis of (1S,2S,5R,6S )-1-hydroxysamin (1) in fewer steps than previously described. 3 Although some synthetic methods for optically active samin are known, 6),7),8) only one stereoselective synthetic route to optically active 1-hydroxysamin (1) has been reported. 3) However, the long pathway for this synthetic method inhibits the production of many synthetic analogues of 1,2-oxygenated 6-arylfurofuran lignan.…”

“…3 Although some synthetic methods for optically active samin are known, 6),7),8) only one stereoselective synthetic route to optically active 1-hydroxysamin (1) has been reported. 3) However, the long pathway for this synthetic method inhibits the production of many synthetic analogues of 1,2-oxygenated 6-arylfurofuran lignan. The many processes for protecting and deprotecting the hydroxy groups result in a lengthy procedure for the synthesis of oxidized lignan.…”