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Synthesis of (±)-Muscopyridine via C-ZIP Ring Enlargement Treatment of 4-(1-nitro-2-oxocyclododec-1-yl)butanal ( 1 ) and of its methyl derivative 5 with pentylamine in EtOH at room temperature gave the ring-enlarged aminomethylidene derivatives 6 and 7 , respectively (Scheme 1). After hydrolysis of the aminomethylidene group in 6 and 7 and deformylation followed by a reductive Nef-type reaction, the macrocyclic diketones 10 and 11 , respectively, were obtained. They were transformed by a modified Hantzsch procedure to the title compound (±)-muscopyridine ( 13 ) and normuscopyridine ( 12 ), respectively. 相似文献
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A Ring Enlargement Reaction with a Barbiturate The (6-membered) barbituric acid derivative 3 was synthesized and treated with KF/DMF/18-crown-6 to form the ring-enlarged 14-membered compound 8 in good yield. 相似文献
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β,γ-unsaturated δ-hydroxy-cyclohexene carboxylic acids undergo a smooth decarboxylative elimination when treated with DMF-dineopentylacetal in an unpolar solvent. The reaction provides a method for the regiospecific preparation of 1,3-cyclohexadiene derivatives under non-isomerizing conditions, starting from easily accessible and structurally variable intermediates. 相似文献
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