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A simple route to methyl 5S-(benzoyloxy)-6-oxohexanoate, a key intermediate in leukotriene synthesis

โœ Scribed by Roy Hayes; Timothy W. Wallace

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
159 KB
Volume
31
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Methyl SS-(benxoyloxy)-6anoate 2, an intermediate in synthetic routes to the lipoxygenasederived arachidonic acid metabolite leukotriene Bh is available in three steps from 2-cyclohexen-l-one, using Schreiber's unsymmetrical oronolysis protocol. Various synthetic routes to the arachidonic acid metabolite leukotriene B4 1' involve the Wittig olefmation of a protected Cl-C6 unit based on 5S-hydroxy-6-oxohexanoic acid. These include the methyl ester-benxoate 2 [prepared from 2-deoxy-D-ribose (6 steps), 2J D-glyceraldehyde acetonide (8 steps),4 cinnamaldehyde (9 steps),5 cyclopentadiene (9 steps),6 or monomethyl glutarate (6 steps)7]. the ethyl ester-benzoate 3 [from 2-

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The X-ray crystal structure of 3~-benzoyloxy-6a-chloro-5a-cholest-7-ene (IV) was determined by the heavy atom method and ref'med to R ---0.063 (space group P2s, a --11.364, b = 11.089, c --12.232,/~ = 99.43 ยฐ, Z ---2). IV was previously shown to be an important intermediate in the acid-catalyzed iso