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

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  →  26  →  27  →  4 ), completes a formal synthesis of digitoxigeni...

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Bibliographic Details
Published in:Canadian journal of chemistry 1989-04, Vol.67 (4), p.580-589
Main Authors: Kutney, James P, Piotrowska, Krystyna, Somerville, John, Huang, Shyh-Pyng, Rettig, Steven J
Format: Article
Language:English
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Summary: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  →  26  →  27  →  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. Keywords: thujone, steroid synthesis, digitoxigenin.
ISSN:0008-4042
1480-3291
DOI:10.1139/v89-088