Stereocontrolled synthesis of 1-acetylen-2,3-di-o-benzyl-tetrahydrofurans, 1,4-anhydro-arabinitol, and alpha,beta-dihydroxy-gamma-alkyl-butyrolactones.
This article describes a concise and efficient synthesis of 1-acetylen-2,3-di-O-benzyl-tetrahydrofurans from tartaric acid esters using as the key step the stereocontrolled cyclization of Co(2)(CO)(6)-complexed propargylic diols. This molecule led to enantiomerically pure 1,4-anhydro-arabinitol and alpha,beta-dihydroxy-gamma-alkyl-butyrolactones. In the latter case, the critical methylene oxidation at the oxygen vicinal position was performed by RuO(4).
Díaz
David D
DD
Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, C/Astrofisico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Spain.
Ramírez
Miguel A
MA
Ceñal
J Pedro
JP
Saad
J Roberto
JR
Tonn
Carlos E
CE
Martín
Victor S
VS
D015107:4-Butyrolactone / Q000138:chemical synthesis*; D002236:Carbohydrate Conformation; D005663:Furans / Q000138:chemical synthesis*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis*; D017975:Ruthenium Compounds / Q000737:chemistry; D013237:Stereoisomerism
D005663:Furans; D009844:Oligosaccharides; D017975:Ruthenium Compounds; C027646:ruthenium tetraoxide; D015107:4-Butyrolactone