Synthesis of [1-¹⁴C] nordolichoic acid

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• 作者：Van Houte ; Hilde A. ; Busson ; Roger H. ; Parmentier ; Guido G. ; Eyssen ; Hendrik J. ; Van Veldhoven ; Paul P. ; et. al.
• 关键词：Polyprenol ; Nordolichoic acid
• 刊名：Chemistry and Physics of Lipids
• 出版年：1996
• 出版时间：July 30, 1996
• 年：1996
• 卷：82
• 期：1
• 页码：79-83
• 全文大小：385 K

文摘

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.