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Synthesis of Idarubicinone via Global Functionalization of Tetracene

preprint
submitted on 30.04.2019, 22:48 and posted on 02.05.2019, 18:29 by David G. Dennis, Mikiko Okumura, David Sarlah
Herein, we describe the realization of this concept, providing a non-annulative strategy to anthracyclines from a polynuclear arene. Specifically, tetracene was converted to idarubicinone, the aglycone of the FDA approved anthracycline idarubicin, through the judicious orchestration of Co- and Ru-catalyzed arene oxidation and arenophile-mediated dearomative hydroboration. Such a global functionalization strategy, a combination of site-selective arene and dearomative functionalization, provided the key anthracycline framework in five operations and enabled rapid and controlled access to idarubicinone.

History

Email Address of Submitting Author

sarlah@illinois.edu

Institution

University of Illinois

Country

USA

ORCID For Submitting Author

0000-0002-8736-8953

Declaration of Conflict of Interest

No conflict of interest

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