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Towards the synthesis of calotropin and related cardenolides from 3-epiandrosterone: A-ring related modifications

Koch, Vanessa; Nieger, Martin; Bräse, Stefan

Abstract:
Calotropin and related cardiac glycosides isolated from plants such as calotropis gigantea represent an interesting target for biological investigations and are based on a cardiac steroid that is doubly connected to a sugar moiety. This naturally occurring family of cardiac glycosides was not only reported to have similar cardiac properties as the drugs digitoxin and digoxin, but also show cytotoxic activity against several cancer cell lines. Herein, the first synthetic access to these molecules is reported highlighting the required transformations of the A-ring of the steroid when starting from commercially available and inexpensive 3-epiandrosterone. Our strategy is based on a regioselective C–H oxidation of the methyl group at C-17 delivering the 2α,3β-trans-diol moiety at the same time and ensuring its connection to the sugar unit.

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Verlagsausgabe §
DOI: 10.5445/IR/1000125414
Veröffentlicht am 28.10.2020
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Institut für Biologische und Chemische Systeme (IBCS)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2020
Sprache Englisch
Identifikator ISSN: 2052-4129
KITopen-ID: 1000125414
HGF-Programm 47.01.01 (POF III, LK 01)
Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Erschienen in Organic chemistry frontiers
Band 7
Heft 18
Seiten 2670–2681
Vorab online veröffentlicht am 14.05.2020
Nachgewiesen in Scopus
Web of Science
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