SYNTHESIS OF 2-SUBSTITUTED 4(R)-HYDROXY-2-CYCLOPENTEN-1-ONE, A PROSTAGLANDIN INTERMEDIATE WITH METHYL OLEATE FROM PALM OIL

摘要

Methyl oleate, 1 was obtained from palm methyl esters through removal of saturated esters in a urea complex formation followed by silver nitrate impregnated silica gel column chrornatography. The oleate was then reacted with 2,3-O-isopropylidene-D-glyceraldehyde 2, to form an aldol compound which, after lactonization, formation of tosylate and cyclic cyanohydrin, and oxidation of the double bond afforded 2-(6-carbomethoxyhexyl)-4(R)-hydroxy-2-cyclopenten-1-one 11, a prostaglandin intermediate.