Synthesis of (+/-)-Muscopyridine via C-ZIP Ring Enlargement

Article abstract of DOI:10.1002/hlca.19920750609

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.