Published February 28, 2019
| Supplemental Material + Published
Journal Article
Open
A modular approach to prepare enantioenriched cyclobutanes: synthesis of (+)-rumphellaone A
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.
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.Attached Files
Published - c8sc05444d.pdf
Supplemental Material - c8sc05444d1.pdf
Supplemental Material - c8sc05444d2.pdf
Files
c8sc05444d1.pdf
Additional details
- PMCID
- PMC6385545
- Eprint ID
- 92078
- Resolver ID
- CaltechAUTHORS:20190104-074958444
- 5T32GM007616-39
- NIH Predoctoral Fellowship
- DGE-1144469
- NSF Graduate Research Fellowship
- Heritage Medical Research Institute
- CHE-1057143
- NSF
- R35GM118191-01
- NIH
- Cottrell Scholar of Research Corporation
- Created
-
2019-01-04Created from EPrint's datestamp field
- Updated
-
2022-02-24Created from EPrint's last_modified field
- Caltech groups
- Heritage Medical Research Institute