Journal of Organic Chemistry p. 1221 - 1228 (1982)
Update date:2022-08-03
Topics:
Jakubowski, Ann A.
Guziec, Frank S.
Sugiura, Marsaru
Tam, Coretta Chan
Tishler, Max
Omura, Satoshi
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.
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Doi:10.1021/ol0702728
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