Kim G,
Chu-Moyer MY,
Danishefsky SJ.
*
Schulte GK.
Yale University, New Haven, USA
The Total Synthesis of Indolizomycin.
J. Am. Chem. Soc. 1993;
115: 30-39
Key words
(±)-indolizomycin - McCluskey fragmentation - Wharton fragmentation
Significance
(±)-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.
Comment
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.
