Total syntheses of (.+-.)-cerulenin,(.+-.)-tetrahydrocerulenin and related compounds

AA Jakubowski, FS Guziec Jr, M Sugiura…

文献索引：Jakubowski, Ann A.; Guziec, Frank S.; Sugiura, Marsaru; Tam, Coretta Chan; Tishler, Max; Omura, Satoshi Journal of Organic Chemistry, 1982 , vol. 47, # 7 p. 1221 - 1228

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被引用次数: 60

摘要

The total Synthesis of the microbial metabolite (&)-cerulenin (1) is described. Detailed evidence for the cyclization of cerulenin to a mixture of hydroxy lactams 2 is presented. The successful synthetic approach to cerulenin uses butenolide 3 as a key intermediate. Sodium hypochlorite in pyridine was found to epoxidize the butenolide system nicely; all other methods investigated failed. The syntheses of (&)-tetrahydrocerulenin 25 and a number of ...