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In this Letter, the first in a series of three, we outline our overall strategy and describe the assembly of a C(29–48) EF-ring advanced intermediate for the total synthesis of the spongistatins, rare and structurally unique polyether macrolides with unprecedented antitumor activity.
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
The C(18–28) CD-ring spiroketal subunit of the spongistatins, marine polyether macrolides with unprecedented antitumor activity, has been generated via a highly convergent and completely stereocontrolled sequence. Key operations include a one-flask dithiane bisalkylation and a metal-assisted spiroketal equilibration.
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSyntheses of Strychnos- and Aspidospermatan-Type Alkaloids. 7. Total Syntheses of Lagunamine, Isolagunamine, Condylocarpine, and IsocondylocarpineMartin E. Kuehne, Christopher S. Brook, Deborah A. Frasier, and Feng XuCite this: J. Org. Chem. 1995, 60, 6, 1864–1867Publication Date (Print):March 1, 1995Publication History Published online1 May 2002Published inissue 1 March 1995https://pubs.acs.org/doi/10.1021/jo00111a053https://doi.org/10.1021/jo00111a053research-articleACS PublicationsRequest reuse permissionsArticle Views437Altmetric-Citations19LEARN 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 (2)»Supporting Information Supporting Information Get e-Alerts
19-Oxodihydroakuammicine was obtained in a three-pot sequence, in 25% overall yield based on a new condensation-sigmatropic rearrangement sequence. Reductions-and quaternization reactions furnished the title compounds.
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Reactions of hetero-substituted acetaldehydes, or ethynyl methyl ketone, or methyl propiolate with methyl 1,2,3,4,5,8-hexahydroazonino[6,7-b]indole-7-carboxylate gave the pentacyclic core of the strychnos alkaloids with substituents on the central bridge.
Total syntheses of racemic dihydromossambine, lagunamine, echitamidine, alstogustine, epi-alstogustine and strychnine were obtained from two alternative synthetic strategies.
Intramolecular Diels-Alder reactions, at two stages in the reaction sequence, provided total syntheses of the racemate of the hypotensive alkaloid echitamidine (8) and of its C-19,20 and C-20 epimers 9a and 9b.