ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTBryostatins revisited: a new bryostatin 3 and the use of NMR to determine stereochemistry in the C-20-C-23 areaGwendolyn N. Chmurny, Mary P. Koleck, and Bruce D. HiltonCite this: J. Org. Chem. 1992, 57, 19, 5260–5264Publication Date (Print):September 1, 1992Publication History Published online1 May 2002Published inissue 1 September 1992https://pubs.acs.org/doi/10.1021/jo00045a049https://doi.org/10.1021/jo00045a049research-articleACS PublicationsRequest reuse permissionsArticle Views129Altmetric-Citations21LEARN 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 Get e-Alerts

During a large‐scale isolation of bryostatin 1, NMR measurements indicated that parts of the published 13 C and 1 H NMR assignments had to be revised. These reassignments were based on extensive homonuclear and heteronuclear one‐ and two‐dimensional NMR techniques performed at 500 MHz. These independently obtained assignments are also in good agreement with the revised assignments and structure of bryostatin 3.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTRevised structure of bryostatin 3 and isolation of the bryostatin 3 26-ketone from Bugula neritina [Erratum to document cited in CA115(3):26268m]Daniel E. Schaufelberger, Gwendolyn N. Chmurny, John A. Beutler, Mary P. Koleck, A. Belinda Alvarado, Brigitte W. Schaufelberger, and Gary M. MuschikCite this: J. Org. Chem. 1991, 56, 19, 5736Publication Date (Print):September 1, 1991Publication History Published online1 May 2002Published inissue 1 September 1991https://pubs.acs.org/doi/10.1021/jo00019a058https://doi.org/10.1021/jo00019a058research-articleACS PublicationsRequest reuse permissionsArticle Views36Altmetric-Citations-LEARN 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

Bryostatin 3 and the corresponding 26-ketone 5, which represents a new bryostatin, were isolated from the marine bryozoan Bugula neritina (Bugulidae). Spectroscopic data from 2D NMR studies indicate that the structure of bryostatin 3 (3) has to be revised to structure 4. Bryostatin 3 showed [H-3]phorbol dibutyrate receptor displacement activity similar to that of bryostatin 1, whereas the corresponding 26-ketone 5 was significantly less active.

A novel process was designed for the large-scale isolation of bryostatin 1 from the bryozoan Bugula neritina L. in order to obtain multigram quantities of highly pure material for formulation studies, preclinical toxicology, and clinical trials in cancer patients. Multigram quantities of bryostatin 1 were obtained from a collection of approximately 10,000 gallons of wet animal. A phorbol dibutyrate (PDBu) receptor binding assay and hplc with photodiode array detection were used for the design, validation, and control of the isolation process.

Condensation of homophthalic anhydride 3 with the Schiff base 4 is exploited as the key step in a total synthesis of the benzophenanthridine alkaloid (±)-chelidonine (8).