@article{d5a86791fffd4af5bbf3b6c80b297141,
title = "Total Synthesis of Lycoricidine and Narciclasine by Chemical Dearomatization of Bromobenzene",
abstract = "The total synthesis of lycoricidine and narciclasine is enabled by an arenophile-mediated dearomative dihydroxylation of bromobenzene. Subsequent transpositive Suzuki coupling and cycloreversion deliver a key biaryl dihydrodiol intermediate, which is rapidly converted into lycoricidine through site-selective syn-1,4-hydroxyamination and deprotection. The total synthesis of narciclasine is accomplished by the late-stage, amide-directed C−H hydroxylation of a lycoricidine intermediate. Moreover, the general applicability of this strategy to access dihydroxylated biphenyls is demonstrated with several examples.",
keywords = "alkaloids, dearomatization, lycoricidine, narciclasine, total synthesis",
author = "Southgate, {Emma H.} and Holycross, {Daniel R.} and David Sarlah",
note = "Funding Information: Financial support for this work was provided by the University of Illinois, the National Science Foundation (CAREER Award No. CHE-1654110), and the ACS Petroleum Research Fund (57175-DNI1). D.S. is an Alfred P. Sloan Fellow. E.H.S. acknowledges a National Institute of General Medical Sciences (NIGMS)-NIH Chemistry-Biology Interface Training Grant as well as a Springborn Graduate Fellowship. We also thank Dr. D. Olson and Dr. L. Zhu for assistance with NMR spectroscopy, Dr. D. L. Gray for assistance with X-ray crystallography, and F. Sun for help with mass spectrometry. Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",
year = "2017",
month = nov,
day = "20",
doi = "10.1002/anie.201709712",
language = "English (US)",
volume = "56",
pages = "15049--15052",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley & Sons, Ltd.",
number = "47",
}