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Total Synthesis of (±)-Indolizomycin
The Total Synthesis of Indolizomycin.
J. Am. Chem. Soc. 1993;
21 July 2020 (online)
(±)-Indolizomycin has a unique structure containing a hemiaminal, where the bridgehead hydroxy group is flanked by a cyclopropane and an epoxide. Danishefsky and co-workers describe the first total synthesis of (±)-indolizomycin.
Annulation of diazo ketone D furnished indolizidine E. Subsequent McCluskey fragmentation and epoxidation set the stage for a Wharton fragmentation to furnish allylic alcohol I. Further elaboration gave (±)-indolizomycin.