80734-34-5Relevant academic research and scientific papers
Total Syntheses of (+/-)-Cerulenin, (+/-)-Tetrahydrocerulenin, and Related Compounds
Jakubowski, Ann A.,Guziec, Frank S.,Sugiura, Marsaru,Tam, Coretta Chan,Tishler, Max,Omura, Satoshi
, p. 1221 - 1228 (1982)
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 related compounds are also described.
