Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
ALKYLATION OF 2,4-DIMETHYL-3-FUROIC ACID AND SYNTHESIS OF 4,6-DIOXO-14-NORFURANOEUDESMANS
Masahiro TadaTakeyoshi Takahashi
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JOURNALS FREE ACCESS

1978 Volume 7 Issue 3 Pages 275-278

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Abstract

Treatment of 2,4-dimethyl-3-furoic acid in THF with LDA gave a dianion (A). Alkylation of A with methyl iodide, cyclohexanone, 2-methyl-2-cyclohexenone or 3-methoxy-2-cyclohexenone yielded the corresponding alkylated derivatives (2, 3, 4 or 5) respectively. The methyl ester (6) was treated with LiMe2Cu to give 4,6-dioxo-14-norfuranoeudesmane (7), a key intermediate for the synthesis of some eudesmanolides and elemanolides.

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