G. SKOKOTAS

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTotal synthesis of hemibrevetoxin B and (7a.alpha.)-epi-hemibrevetoxin BK. C. Nicolaou, K. Raja Reddy, Golfo Skokotas, Fuminori Sato, Xiao Yi Xiao, and C. K. HwangCite this: J. Am. Chem. Soc. 1993, 115, 9, 3558–3575Publication Date (Print):May 1, 1993Publication History Published online1 May 2002Published inissue 1 May 1993https://pubs.acs.org/doi/10.1021/ja00062a021https://doi.org/10.1021/ja00062a021research-articleACS PublicationsRequest reuse permissionsArticle Views1309Altmetric-Citations104LEARN 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 (3)»Supporting Information Supporting Information Get e-Alerts

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTotal synthesis of hemibrevetoxin BK. C. Nicolaou, K. Raja Reddy, Golfo Skokotas, Fuminori Sato, and Xiao Yi XiaoCite this: J. Am. Chem. Soc. 1992, 114, 20, 7935–7936Publication Date (Print):September 1, 1992Publication History Published online1 May 2002Published inissue 1 September 1992https://pubs.acs.org/doi/10.1021/ja00046a063https://doi.org/10.1021/ja00046a063research-articleACS PublicationsRequest reuse permissionsArticle Views939Altmetric-Citations68LEARN 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

DNA-cleaving agents are of considerable interest in molecular biology and pharmaceutical chemistry. The Garrett–Braverman reaction sequence has now been utilized as a basis for developing the title compounds; l–3 are examples. They are capable of cleaving ϕX174 DNA in a pH-dependent reaction with maximal activity at pH 8.5.

Retroaldol reaction, propargyl–allenyl isomerization, and [4 + 2] cycloaddition are the steps involved in the reaction of the title compound 1 with 1,8-diazabi-cyclo[5.4.0]undec-7-ene at room temperature in THF. The product 2, like 1, reacts readily with nucleophiles such as methyl thioglycolate. The biological activity of these compounds is presumably due to this reactivity.

DNA‐angreifende Agentien sind für die Molekularbiologie und für die Pharmazeutische Chemie von großem Interesse. Auf der Basis der Garrett‐Braverman‐Reaktionssequenz wurden nun die Titelverbindungen entwickelt; 1–3 sind Beispiele. Sie können ΦX174‐DNA pH‐abhängig spalten (maximale Aktivität bei pH 8.5). magnified image