0000000000977444
AUTHOR
Purificación Ruiz
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.
Stereoselective anti aldol reactions of erythrulose derivatives. Functionalized chiral d3 and d4 synthons.
An improved procedure for the synthesis of anti aldols from protected erythrulose derivatives is reported. The preparation of functionalized d3 and d4 synthons with various stereochemical arrays by means of this methodology is described and subsequently applied to a stereoselective formal synthesis of the natural metabolite goniothalesdiol.