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A modular approach to prepare enantioenriched cyclobutanes: synthesis of (+)-rumphellaone A

Beck, Jordan C. and Lacker, Caitlin R. and Chapman, Lauren M. and Reisman, Sarah E. (2019) A modular approach to prepare enantioenriched cyclobutanes: synthesis of (+)-rumphellaone A. Chemical Science, 10 (8). pp. 2315-2319. ISSN 2041-6520. PMCID PMC6385545. http://resolver.caltech.edu/CaltechAUTHORS:20190104-074958444

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Abstract

A modular synthesis of enantioenriched polyfunctionalized cyclobutanes was developed that features an 8-aminoquinolinamide directed C–H arylation reaction. The C–H arylation products were derivatized through subsequent decarboxylative coupling processes. This synthetic strategy enabled a 9-step enantioselective total synthesis of the antiproliferative meroterpenoid (+)-rumphellaone A.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1039/c8sc05444dDOIArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6385545PubMed CentralArticle
ORCID:
AuthorORCID
Beck, Jordan C.0000-0003-0898-5644
Lacker, Caitlin R.0000-0003-2531-2636
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© The Royal Society of Chemistry 2018. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Received 6th December 2018. Accepted 19th December 2018. We thank Dr Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. Fellowship support was provided by an NIH Training Grant (J. C. B., Grant No. 5T32GM007616-39) and the NSF (C. R. L. and L. M. C., Grant No. DGE-1144469) and. S. E. R. is a Heritage Medical Research Foundation Investigator. Partial financial support from the NSF (CAREER-1057143) and NIH (R35GM118191-01), as well as the Research Corporation Cottrell Scholars program, is gratefully acknowledged. Conflicts of interest: There are no conflicts to declare. All publication charges for this article have been paid for by the Royal Society of Chemistry.
Group:Heritage Medical Research Institute
Funders:
Funding AgencyGrant Number
NIH Predoctoral Fellowship5T32GM007616-39
NSF Graduate Research FellowshipDGE-1144469
Heritage Medical Research InstituteUNSPECIFIED
NSFCHE-1057143
NIHR35GM118191-01
Cottrell Scholar of Research CorporationUNSPECIFIED
PubMed Central ID:PMC6385545
Record Number:CaltechAUTHORS:20190104-074958444
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20190104-074958444
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:92078
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:04 Jan 2019 17:43
Last Modified:18 Mar 2019 15:31

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