Short syntheses of gabosine I and gabosine G from delta-D-gluconolactone.
A short synthesis of gabosine I (1) from delta-D-gluconolactone (3) in four steps, involving a one-pot TPAP oxidation-K2CO3-mediated intramolecular Horner-Wadsworth-Emmons (HWE) olefination as the key step, is described. Regioselective acetylation of the primary alcohol in gabosine I (1) then furnished gabosine G (2).
Shing
Tony K M
TK
Department of Chemistry and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, Hong Kong, China. tonyshing@cuhk.edu.hk
Cheng
Hau M
HM
D003512:Cyclohexanones / Q000138:chemical synthesis*; D005942:Gluconates / Q000737:chemistry*; D007783:Lactones; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D016339:Spectrometry, Mass, Fast Atom Bombardment
D003512:Cyclohexanones; D005942:Gluconates; D007783:Lactones; C523707:gabosine G; C523708:gabosine I; C010730:beta-glucono-1,5-lactone