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Total Synthesis of (+)-Pleuromutilin.


ABSTRACT: 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.

SUBMITTER: Farney EP 

PROVIDER: S-EPMC5988231 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Total Synthesis of (+)-Pleuromutilin.

Farney Elliot P EP   Feng Sean S SS   Schäfers Felix F   Reisman Sarah E SE  

Journal of the American Chemical Society 20180117 4


An 18-step synthesis of the antibiotic (+)-pleuromutilin is disclosed. The key steps of the synthesis include a highly stereoselective SmI<sub>2</sub>-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. ...[more]

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