3 years ago

Total Synthesis of (+)-Pleuromutilin

Synthesis of (+)-Pleuromutilin
Sean S. Feng, Sarah E. Reisman, Felix Schäfers, Elliot P. Farney
An 18-step synthesis of the antibiotic (+)-pleuromutilin is disclosed. The key steps of the synthesis include a highly stereoselective SmI2-mediated cyclization to establish the eight-membered ring and a stereospecific transannular [1,5]-hydrogen atom transfer to set the C10 stereocenter. This strategy was also used to prepare (+)-12-epi-pleuromutilin. The chemistry described here will enable efforts to prepare new mutilin antibiotics.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b13260

DOI: 10.1021/jacs.7b13260

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