Three-Component One-Pot Total Syntheses of Glyantrypine, Fumiquinazoline F, and Fiscalin B Promoted by Microwave Irradiation
A microwave-promoted three-component one-pot reaction has been developed to provide access to the core pyrazino[2,1-b]quinazoline-3,6-dione (1) scaffold, which is common to several families of alkaloids with significant biological activities. By adapting this synthetic strategy through the use of se...
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| Veröffentlicht in: | Journal of organic chemistry 2005-08, Vol.70 (16), p.6339-6345 |
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| container_issue | 16 |
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| container_title | Journal of organic chemistry |
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| creator | Liu, Ji-Feng Ye, Ping Zhang, Bailin Bi, Grace Sargent, Katie Yu, Libing Yohannes, Daniel Baldino, Carmen M |
| description | A microwave-promoted three-component one-pot reaction has been developed to provide access to the core pyrazino[2,1-b]quinazoline-3,6-dione (1) scaffold, which is common to several families of alkaloids with significant biological activities. By adapting this synthetic strategy through the use of selected Boc-amino acids and amino acid esters, we have accomplished highly efficient and concise total syntheses of glyantrypine (2), fumiquinazoline F (3), and fiscalin B (5), achieving overall yields of 55, 39, and 20%, respectively. |
| doi_str_mv | 10.1021/jo0508043 |
| format | Article |
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Org. Chem</addtitle><description>A microwave-promoted three-component one-pot reaction has been developed to provide access to the core pyrazino[2,1-b]quinazoline-3,6-dione (1) scaffold, which is common to several families of alkaloids with significant biological activities. 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Ye, Ping ; Zhang, Bailin ; Bi, Grace ; Sargent, Katie ; Yu, Libing ; Yohannes, Daniel ; Baldino, Carmen M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-de8896668678a61adc70d0c82b0f229a6b7d9517cd6fcd1eea586a90b80dde613</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Alkaloids - chemistry</topic><topic>Biological Factors - chemistry</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Mass Spectrometry</topic><topic>Microwaves</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Quinazolines - chemical synthesis</topic><topic>Quinazolines - chemistry</topic><topic>Tryptophan - analogs & derivatives</topic><topic>Tryptophan - chemical synthesis</topic><topic>Tryptophan - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Ji-Feng</creatorcontrib><creatorcontrib>Ye, Ping</creatorcontrib><creatorcontrib>Zhang, Bailin</creatorcontrib><creatorcontrib>Bi, Grace</creatorcontrib><creatorcontrib>Sargent, Katie</creatorcontrib><creatorcontrib>Yu, Libing</creatorcontrib><creatorcontrib>Yohannes, Daniel</creatorcontrib><creatorcontrib>Baldino, Carmen M</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Ji-Feng</au><au>Ye, Ping</au><au>Zhang, Bailin</au><au>Bi, Grace</au><au>Sargent, Katie</au><au>Yu, Libing</au><au>Yohannes, Daniel</au><au>Baldino, Carmen M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Three-Component One-Pot Total Syntheses of Glyantrypine, Fumiquinazoline F, and Fiscalin B Promoted by Microwave Irradiation</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2005-08-05</date><risdate>2005</risdate><volume>70</volume><issue>16</issue><spage>6339</spage><epage>6345</epage><pages>6339-6345</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A microwave-promoted three-component one-pot reaction has been developed to provide access to the core pyrazino[2,1-b]quinazoline-3,6-dione (1) scaffold, which is common to several families of alkaloids with significant biological activities. By adapting this synthetic strategy through the use of selected Boc-amino acids and amino acid esters, we have accomplished highly efficient and concise total syntheses of glyantrypine (2), fumiquinazoline F (3), and fiscalin B (5), achieving overall yields of 55, 39, and 20%, respectively.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16050695</pmid><doi>10.1021/jo0508043</doi><tpages>7</tpages></addata></record> |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Alkaloids - chemistry Biological Factors - chemistry Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Indoles - chemical synthesis Indoles - chemistry Mass Spectrometry Microwaves Molecular Structure Organic chemistry Preparations and properties Quinazolines - chemical synthesis Quinazolines - chemistry Tryptophan - analogs & derivatives Tryptophan - chemical synthesis Tryptophan - chemistry |
| title | Three-Component One-Pot Total Syntheses of Glyantrypine, Fumiquinazoline F, and Fiscalin B Promoted by Microwave Irradiation |
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