RESEARCH ARTICLE

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

MUHAMMAD NOR Omar* ; HAMILTON, R J**

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.