What question did this study set out to answer?

To achieve the stereoselective total synthesis of the natural cardenolide (+)-digitoxigenin using controlled multi-step organic synthesis.

January 1, 1996Journal of the American Chemical Society

The Total Synthesis of a Natural Cardenolide: (+)-Digitoxigenin

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To achieve the stereoselective total synthesis of the natural cardenolide (+)-digitoxigenin using controlled multi-step organic synthesis.
Designed a convergent multi-step route centered on aldehyde intermediates and stereocontrolled cyclization sequences.
Assembled the tetracyclic steroid core and introduced the signature C17 butenolide lactone ring characteristic of cardenolide aglycones.
Completed the de novo total synthesis of naturally occurring (+)-digitoxigenin in its enantiomerically pure form.
Established a versatile synthetic framework adaptable for constructing diverse cardenolides and related cardiac glycoside derivatives.

Implication

Synthetic chemistry study demonstrates the total synthesis of (+)-digitoxigenin, highlighting efficient stereocontrolled cyclization routes to natural cardenolides.

Abstract

ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTThe Total Synthesis of a Natural Cardenolide: (+)-DigitoxigeninGilbert Stork, Fred West, Hee Yoon Lee, Richard C. A. Isaacs, and Shino ManabeView Author Information Department of Chemistry, Columbia University New York, New York 10027 Cite this: J. Am. Chem. Soc. 1996, 118, 43, 10660–10661Publication Date (Web):October 30, 1996Publication History Received26 June 1996Published online30 October 1996Published inissue 1 January 1996https://pubs.acs.org/doi/10.1021/ja962163mhttps://doi.org/10.1021/ja962163mrapid-communicationACS PublicationsCopyright © 1996 American Chemical SocietyRequest reuse permissionsArticle Views4129Altmetric-Citations86LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Aldehydes,Chemical synthesis,Cyclization,Organic synthesis,Substituents Get e-Alerts

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Cite This Study

Stork et al. (1996) studied this question.

synapsesocial.com/papers/6a911e95c9591f682e830843 https://doi.org/10.1021/ja962163m

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Implication

Synthetic chemistry study demonstrates the total synthesis of (+)-digitoxigenin, highlighting efficient stereocontrolled cyclization routes to natural cardenolides.

The Total Synthesis of a Natural Cardenolide: (+)-Digitoxigenin

Key Points

Implication

Abstract

Discussion

Cite This Study

The Total Synthesis of a Natural Cardenolide: (+)-Digitoxigenin

Key Points

Implication

Abstract

Discussion

Cite This Study

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