Synthesis of 2-substituted 4(R)-hydroxy-2-cyclopenten-1-one, a prostaglandin intermediate with methyl oleate from palm oil

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, af...

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Bibliographic Details
Main Authors: Omar, Muhammad Nor, Hamilton, Richard J.
Format: Article
Language:English
Published: Malaysian Palm Oil Board 2004
Subjects:
Online Access:http://irep.iium.edu.my/24442/
http://irep.iium.edu.my/24442/
http://irep.iium.edu.my/24442/1/Dr_NO_prostaglandin_article.pdf
Description
Summary: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.