Issue 8, 2019

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
06 Dec. 2018
Accepted
19 Dec. 2018
First published
19 Dec. 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 2315-2319

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

J. C. Beck, C. R. Lacker, L. M. Chapman and S. E. Reisman, Chem. Sci., 2019, 10, 2315 DOI: 10.1039/C8SC05444D

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