Oxidation products of arachidonic acid II. The synthesis of methyl 8R,9S,11R-trihydroxy-5Z,12E,14Z-eicosatrienoate
- 1 September 1980
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 58 (17) , 1799-1805
- https://doi.org/10.1139/v80-284
Abstract
A stereospecific total synthesis of the title compound, 37, starting from diacetone glucose (9), is described. Key intermediates in the synthesis are 3-deoxy-5,6-anhydro-1,2-O-isopropylidene-glucofuranose (15), obtained in 55% yield from 9, and methyl 8-tert-butyldiphenylsilyl-9,11-O-isopropylidene-8R,9S,11R-trihydroxy-12-oxo-dodeca-5Z-enoate (33), an important intermediate in the synthesis of other oxidation products of arachidonic acid.This publication has 3 references indexed in Scilit:
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- On the Mechanism of the Biosynthesis of Prostaglandins E1 and F1αJournal of Biological Chemistry, 1967