ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
0/0

Synthesis of Idarubicinone via Global Functionalization of Tetracene

preprint
submitted on 30.04.2019 and posted on 02.05.2019 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

Exports