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A new simple route to furanic ketones; Preparation of Elsholtzione, naginata ketone and perilla ketone.

✍ Scribed by Gérard Cahiez; Pierre-Yves Chavant; Eric Metais

Book ID
104215794
Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
275 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis

Copper-or iron-catalyzed aqlation of organomanganese reagents allows to obtain 3-and 2-acylfurans in high yields. Elsholtzione, naginata ketone and perilla ketone have been prepared according to this procedure.

Recently, we have shown that a vast array of ketones can be easily prepared in high yields by acylation of organomanganese reagentsz. Now, we report an application of this method to the synthesis of three natural furanic ketones? elsholtzione 34, naginata ketone 45 and perilla ketone 66.

Elsholtzione 3 and naginata ketone 4 were prepared according to Scheme I. The synthesis of the starting ethyl 3-methyl-2-furoate 1 has already been described'. Saponification of 1, then treatment of the crude carboxylic acid thus obtained with thionyl chloride, afforded 3-methylfuroyl chloride 2. Acylation, under mild

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