On cardioactive steroids. IV. A new synthesis of cardenolides

Marini-Bettolo, R.; Flecker, Petr; Tsai, T. Y. R.; Wiesner, K.

doi:10.1139/v81-206

Cited by 13 publications

(2 citation statements)

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“…The furan methodology of Wiesner and Tsai, [6,29] first described in the early 1980s, remains perhaps the most practical and advantageous strategy for the conversion of testosterone derivatives (17-oxoandrostanes) into cardenolides. The two major stereochemical problems associated with this task, introduction of 17b substituents and the 14b hydroxyl, are nicely addressed using simple and inexpensive reagents.…”

Section: Partial Synthesis Of Cardenolidesmentioning

confidence: 99%

Chemical Synthesis of the Cardiotonic Steroid Glycosides and Related Natural Products

Heasley

2012

Chemistry A European J

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The active components from the extracts of Digitalis, cardiotonic steroid glycosides, have been ingested by humans for more than 200 years as a medicinal therapy for heart failure and abnormal heart rhythms. The positive inotropic activity of the cardiotonic steroids that mediates clinically useful physiological effects in patients has been attributed largely to a high affinity inhibitory interaction with the extracellular surface of the membrane-bound sodium pump (Na(+)/K(+)-ATPase). However, previously unrecognized intracellular signaling pathways continue to be uncovered. This Review examines both partial and de novo synthetic approaches to the medicinally important and structurally captivating cardenolide and bufadienolide steroid families, with an emphasis on the stereocontrolled construction of the pharmacophoric aglycone (genin) framework.

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Section: Partial Synthesis Of Cardenolidesmentioning

confidence: 99%

Chemical Synthesis of the Cardiotonic Steroid Glycosides and Related Natural Products

Heasley

2012

Chemistry A European J

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“…Previous synthetic studies in various laboratories (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) have afforded synthetic routes to this series of compounds. In these studies, steroidal starting materials were employed and different routes to the butenolide ring system, characteristic of this family of natural products, were developed.…”

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confidence: 99%

The chemistry of thujone. XIII. Synthetic studies in the digitoxigenin series

Kutney¹,

Piotrowska²,

Somerville³

et al. 1989

Can. J. Chem.

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. J. Chem. 580 (1989). 67,The thujone-derived chiral synthon 1 is converted, via selenium chmistry, to the important cross-conjugated dienone 2 and the latter is then convertible to the unsaturated cardenolide analogue 3, which through known methodology (3 4 26 4 27 4 4), completes a formal synthesis of digitoxigenin (4). Extensive studies to afford 2 from androstenedione (5) are also described and a new approach to elaborate the essential butenolide ring system, characteristic of the cardiac active steroids, is developed.Key words: thujone, steroid synthesis, digitoxigenin.JAMES P. KUTNEY, KRYSTYNA PIOTROWSKA, JOHN SOMERVILLE, SHYH-PYNG HUANG et STEVEN J. RETTIG. Can. J. Chem. 67, 580 (1989).En utilisant la chimie du sClCnium, on a transforme le synthon chiral 1, obtenu a partir de la thujone, en la dienone importante 2 % conjugaison croisCe que l'on peut convertir en analogue cardenolide insaturC 3; ce composk, par le biais d'une mCthodologie connue (3 4 26 4 27 4 4), donne lieu a une synthkse formelle de la digitoxigknine (4). On dCcrit aussi les Ctudes poussCes qui ont Ct C effectuCes pour obtenir le composC 2 i partir de l'androstknedione (5) et on a dCveloppC une nouvelle approche au systkme cyclique butCnolide essentiel, caractCristique des stCroi'des actifs au niveau cardiaque.

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