Synthesis of [1-14C]nordolichoic acid

Synthesis of [1-14C]nordolichoic acid

We describe the synthesis of nordolichoic acid and [1-14C]nordolichoic acid starting from polyprenol isolated from the leaves of Ginkgo biloba. Coupling of polyprenol with ethyl acetoacetate, using 1,1'-(azodicarbonyl)dipiperidine/tributylphosphine, followed by hydrolysis, decarboxylation and r...

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Veröffentlicht in:Chemistry and physics of lipids 1996, Vol.82 (1), p.79-83
Hauptverfasser: Van Houte, H.A, Busson, Roger, Parmentier, Guido, Eyssen, Hendrik, Van Veldhoven, Paul P, Mannaerts, Guy, Baes, Myriam, Declercq, Peter
Format: Artikel
Sprache:eng
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Zusammenfassung:We describe the synthesis of nordolichoic acid and [1-14C]nordolichoic acid starting from polyprenol isolated from the leaves of Ginkgo biloba. Coupling of polyprenol with ethyl acetoacetate, using 1,1'-(azodicarbonyl)dipiperidine/tributylphosphine, followed by hydrolysis, decarboxylation and reduction, yielded the 2-polyprenyl-1-methylethanol. This alcohol was converted into a mesylate, subjected to one-carbon elongation with KCN, and finally converted to the acid by hydrolysis of the nitrile.
ISSN:0009-3084