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Total Synthesis of (+)-Pleuromutilin

Farney, Elliot P. and Feng, Sean S. and Schäfers, Felix and Reisman, Sarah E. (2018) Total Synthesis of (+)-Pleuromutilin. Journal of the American Chemical Society, 140 (4). pp. 1267-1270. ISSN 0002-7863. PMCID PMC5988231. https://resolver.caltech.edu/CaltechAUTHORS:20180112-131323403

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/jacs.7b13260DOIArticle
https://pubs.acs.org/doi/suppl/10.1021/jacs.7b13260PublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5988231PubMed CentralArticle
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2018 American Chemical Society. Received: December 15, 2017; Published: January 11, 2018. We thank Dr. Michael Takase and Larry Henling for X-ray data collection, Ms. Julie Hofstra for X-ray data refinement, Dr. David VanderVelde for assistance with NMR structure determination, Dr. Scott Virgil for assistance with crystallization of 26, and the Caltech 3CS for access to analytical equipment. Fellowship support was provided by the NIH (E.P.F., Grant 1F32GM117764) and NSF (S.S.F., DGE-1144469). Financial support from the Heritage Medical Research Institute is gratefully acknowledged. The authors declare no competing financial interest.
Group:Heritage Medical Research Institute
Funders:
Funding AgencyGrant Number
NIH Postdoctoral FellowshipF32GM117764
NSF Graduate Research FellowshipDGE-1144469
Heritage Medical Research InstituteUNSPECIFIED
Issue or Number:4
PubMed Central ID:PMC5988231
Record Number:CaltechAUTHORS:20180112-131323403
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180112-131323403
Official Citation:Total Synthesis of (+)-Pleuromutilin. Elliot P. Farney, Sean S. Feng, Felix Schäfers, and Sarah E. Reisman. Journal of the American Chemical Society 2018 140 (4), 1267-1270. DOI: 10.1021/jacs.7b13260
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:84305
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:16 Jan 2018 16:38
Last Modified:03 Oct 2019 19:17

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