Journal of Oil Palm Research Vol. 16 No. 2, December 2004, p. 37-43
SYNTHESIS OF 2-SUBSTITUTED 4(R)-HYDROXY-2-CYCLOPENTEN-1-ONE, A PROSTAGLANDIN INTERMEDIATE WITH METHYL OLEATE FROM PALM OIL
ABSTRACT
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 chromatography. 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
KEYWORDS:* Malaysian Palm Oil Board,
P. O. Box 10620,
50720 Kuala Lumpur, Malaysia.
E-mail: mohdnor@mpob.gov.my
** School of Pharmacy and Chemistry,
Liverpool John Moores University, Byrom Street,
Liverpool L3 3AF, United Kingdom.