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Synfacts 2020; 16(08): 0891
DOI: 10.1055/s-0040-1707087
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (±)-Indolizomycin

Contributor(s):
Erick M. Carreira
,
Hendrik Bulthaupt
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
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Further Information

Publication History

Publication Date:
21 July 2020 (online)

 
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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.


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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.


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