Stereoselective synthesis of the naturally occurring styryllactones (+)-goniofufurone and (+)-cardiobutanolide.
The naturally occurring gamma-lactones (+)-goniofufurone 1 and (+)-cardiobutanolide 2, two pharmacologically active products from Goniothalamus species (Annonaceae), have been synthesized in enantiopure form using l-erythrulose as the chiral starting material. Key steps of these syntheses were a stereoselective anti boron aldol reaction and an asymmetric allylboration.
Ruiz
Purificación
P
Departamento de Química Inorgánica y Orgánica, Universidad Jaume I, E-12071 Castellón, Spain, and Departamento de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Valencia, Spain.
Murga
Juan
J
Carda
Miguel
M
Marco
J Alberto
JA
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D029061:Annonaceae / Q000737:chemistry*; D005990:Glycerol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D007783:Lactones; C472942:cardiobutanolide; C073080:7-goniofufurone; D015107:4-Butyrolactone; D005990:Glycerol