Canadian Journal of Chemistry

Oxidation products of arachidonic acid II. The synthesis of methyl 8 R, 9 S, 11 R-trihydroxy-5 Z, 12 E, 14 Z-eicosatrienoate

G Just, C Luthe

Index: Just, George; Luthe, Corinne Canadian Journal of Chemistry, 1980 , vol. 58, # 17 p. 1799 - 1805

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Citation Number: 27

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-8 R, 9 S, 11 R-trihydroxy-12-oxo-dodeca-5 Z- enoate (33), an important intermediate in the synthesis of other oxidation products of ...

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