Viability of a [2 + 2 + 1] Hetero-Pauson–Khand Cycloaddition Strategy toward Securinega Alkaloids: Synthesis of the BCD-Ring Core of Securinine and Related Alkaloids

Preliminary results related to the development of [2 + 2 + 1]-oxa-hetero-Pauson–Khand cycloaddition strategy toward the Securinega alkaloids are reported. The critical tricyclic BCD-ring core was assembled in only nine linear steps from cheap 4-hydroxy-l-proline. The study provides valuable insight...

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Veröffentlicht in:	Journal of organic chemistry 2015-07, Vol.80 (13), p.6525-6528
Hauptverfasser:	Chirkin, Egor, Michel, Sylvie, Porée, François-Hugues
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemical synthesis Alkaloids - chemistry Azepines - chemical synthesis Azepines - chemistry Biological Products - chemical synthesis Biological Products - chemistry Cycloaddition Reaction Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Heterocyclic Compounds, Bridged-Ring - chemical synthesis Heterocyclic Compounds, Bridged-Ring - chemistry Hydroxyproline - chemistry Lactones - chemical synthesis Lactones - chemistry Piperidines - chemical synthesis Piperidines - chemistry
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container_end_page	6528
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container_title	Journal of organic chemistry
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creator	Chirkin, Egor Michel, Sylvie Porée, François-Hugues
description	Preliminary results related to the development of [2 + 2 + 1]-oxa-hetero-Pauson–Khand cycloaddition strategy toward the Securinega alkaloids are reported. The critical tricyclic BCD-ring core was assembled in only nine linear steps from cheap 4-hydroxy-l-proline. The study provides valuable insight into the scope of a rare hetero-Pauson–Khand reaction, a powerful tool for the rapid construction of butenolide-containing natural products.
doi_str_mv	10.1021/acs.joc.5b01118
format	Article
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Org. Chem</addtitle><date>2015-07-02</date><risdate>2015</risdate><volume>80</volume><issue>13</issue><spage>6525</spage><epage>6528</epage><pages>6525-6528</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Preliminary results related to the development of [2 + 2 + 1]-oxa-hetero-Pauson–Khand cycloaddition strategy toward the Securinega alkaloids are reported. The critical tricyclic BCD-ring core was assembled in only nine linear steps from cheap 4-hydroxy-l-proline. The study provides valuable insight into the scope of a rare hetero-Pauson–Khand reaction, a powerful tool for the rapid construction of butenolide-containing natural products.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26098882</pmid><doi>10.1021/acs.joc.5b01118</doi><tpages>4</tpages></addata></record>
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subjects	Alkaloids - chemical synthesis Alkaloids - chemistry Azepines - chemical synthesis Azepines - chemistry Biological Products - chemical synthesis Biological Products - chemistry Cycloaddition Reaction Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Heterocyclic Compounds, Bridged-Ring - chemical synthesis Heterocyclic Compounds, Bridged-Ring - chemistry Hydroxyproline - chemistry Lactones - chemical synthesis Lactones - chemistry Piperidines - chemical synthesis Piperidines - chemistry
title	Viability of a [2 + 2 + 1] Hetero-Pauson–Khand Cycloaddition Strategy toward Securinega Alkaloids: Synthesis of the BCD-Ring Core of Securinine and Related Alkaloids
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