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AbstractDiels‐Alder reaction of the cycloalkenones (I) with 1,3‐cyclohexadiene (II) produces the endo‐cycloadducts (III).

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPreparation and H(3) isomerization of C(15)-substituted deplancheine derivatives. Synthesis of geissoschizol and geissoschizineErnest Wenkert, Ming Guo, Mauricio J. Pestchanker, Yao Jun Shi, and Yashwant D. VankarCite this: J. Org. Chem. 1989, 54, 5, 1166–1174Publication Date (Print):March 1, 1989Publication History Published online1 May 2002Published inissue 1 March 1989https://pubs.acs.org/doi/10.1021/jo00266a032https://doi.org/10.1021/jo00266a032research-articleACS PublicationsRequest reuse permissionsArticle Views626Altmetric-Citations35LEARN 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-Alertsclose Get e-Alerts

AbstractFurans with side‐chains at C(2) of various lengths terminating in diazomethyl keto groups are shown to undergo Rh2(OAc)4‐catalyzed furan unravelling with the production of 2‐cyclopentenone, 2‐cyclohexenone, and 2‐cycloheptenone to each of whose olefinic C(β) is attached an acrylaldehyde unit. Interposition of a cyclohexane or a methylaminomethylene moiety between the furan and diazoketo functions leads to the formation of a hydroindenone and pyrrolone, respectively. Replacement of the diazomethylketo terminus by an α‐diazoethylketo system or a α‐diazo‐β‐keto‐ester function produces 2‐substituted 2‐cycloalkenones. A furan with a C4, diazo‐methylketo‐terminating side‐chain at C(3) is described to be transformed into a 4‐formylmethylidene‐2‐cyclohe‐xenone.