Abstract
Four enantiomeric forms of natural prostaglandins, ent-PGF2α ((−)-1), ent-PGE2 ((+)-2) ent-PGF1α ((−)-3), and ent-PGE1 ((+)-4) have been synthetized in gram scale by Corey synthesis used in the prostaglandin plants of CHINOIN, Budapest. Chiral HPLC methods have been developed to separate the enantiomeric pairs. Enantiomers of natural prostaglandins can be used as analytical standards to verify the enantiopurity of synthetic prostaglandins, or as biomarkers to study oxidation processes in vivo.
Highlights
Interest in the field of prostaglandins has been steadily growing since the basic work of Bergström Samuelsson, and Vane [1–3]
Four enantiomeric forms of natural prostaglandins, ent-PGF2α ((−)-1), ent-PGE2 ((+)-2) ent-PGF1α ((−)-3), and ent-PGE1 ((+)-4) have been synthetized in gram scale by Corey synthesis used in the prostaglandin plants of CHINOIN, Budapest
The starting material was the ent-Corey lactone ((+)-5), which is a side-product of our prostaglandin production
Summary
Interest in the field of prostaglandins has been steadily growing since the basic work of Bergström Samuelsson, and Vane [1–3]. Their discoveries revealed the structure, the enzyme-controlled biochemical synthesis from arachidonic acid, and the main physiological effects of prostaglandins as well as their related substances. The key intermediate in the synthesis is lactone (−)-5, commonly referred to as Corey lactone, from which the omega and the alpha side chains of prostaglandins can be constructed [8–10]. Noyori developed the idea of the shortest, highly convergent synthesis, the three-component coupling reaction. Aggarwal has developed a short, stereocontrolled organocatalytic synthesis starting with the double aldol reaction of succinaldehyde in the presence of a chiral auxiliary.
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