Abstract
Triacetic lactone ( 1) on treatment with two or more equivs of alkali amides in liquid ammonia was converted into dianion 8. Treatment of 8 with benzyl chloride and other alkyl halides gave mixtures of 6α- and 5-alkylation products 9 and 10. Benzophenone condensed with 8 to give 6α-aldol product 14, which was readily dehydrated to form unsaturated pyrone 15. 6α-Carboxylation of dilithio 8, which had been formed in THF by treatment of 1 with lithium diisopropylamide, was also effected. Aroylation of 8 with methyl benzoate gave 6-phenacyl pyrone 17, but acetylation of 8 was not successful. Two monomethylation ( 18 and 24) and three dimethylation ( 19–21) products of 17 were prepared and identified. Condensation of 17 with malonyl chloride gave pyranopyran 25.
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