Synthesis of heterocyclic platelet activating factor analogues

Article abstract of DOI:10.1016/0009-3084(95)93676-6

The synthesis of heterocyclic analogues of the platelet activating factor is described.The preparation starts with acylating rac-tetrahydro-1,3-thiazine-4-carboxylic acid ethyl ester, with palmitoyl chloride to form the amide linkage.Following ester reduction, the phosphocholine part is introduced via 2-chloro-2-oxo-1,3,2-dioxaphospholane and subsequent ring opening with trimethylamine under pressure.Furthermore, the related L-thiazolidine analogue is prepared using the same procedure.In addition the sulfinyl and sulfonyl derivatives of this compound are obtained by oxidation with 3-chloro-perbenzoic acid.From one sulfinyl intermediate the diastereomeres are separated and their conformations are determined by 13C-NMR spectroscopy. Keywords: Phospholipid synthesis; Cyclic platelet activating factor analogue; Cyclic thioether; Chiral sulphur compound