Regioselective and diastereoselective amination of polybenzyl ethers using chlorosulfonyl isocyanate: total syntheses of 1,4-dideoxy-1,4-imino-D-arabinitol and (-)-lentiginosine.
The total syntheses of DAB1 (1) and (-)-lentiginosine (2) were concisely accomplished from D-lyxose via regioselective and diastereoselective NHCbz introduction using CSI, chemoselective removal of the Cbz protection, and ring-closing metathesis as key steps.
Kim
In Su
IS
College of Pharmacy, Sungkyunkwan University, Suwon 440-746, Korea.
Zee
Ok Pyo
OP
Jung
Young Hoon
YH
D000470:Alkaloids / Q000138:chemical synthesis*; D000586:Amination; D001089:Arabinose; D004987:Ethers / Q000737:chemistry*; D050113:Imino Furanoses; D017953:Isocyanates / Q000737:chemistry*; D015394:Molecular Structure; D013402:Sugar Alcohols / Q000138:chemical synthesis*
D000470:Alkaloids; D004987:Ethers; D050113:Imino Furanoses; D017953:Isocyanates; D013402:Sugar Alcohols; C487390:chlorosulfonyl isocyanate; C058137:1,4-dideoxy-1,4-iminoarabinitol; C063984:lentiginosine; D001089:Arabinose