Isocomplestatin: Total Synthesis and Stereochemical Revision
A Pd-mediated method for preparation of the strained macrocyclic moiety of complestatins is disclosed. Through stereoselective synthesis of model macrocycles and the S atropisomer of complestatin, the stereochemical identity of the anti-HIV agent complestatin is established. Investigations described...
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| Veröffentlicht in: | Journal of the American Chemical Society 2005-05, Vol.127 (20), p.7334-7336 |
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| container_end_page | 7336 |
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| container_issue | 20 |
| container_start_page | 7334 |
| container_title | Journal of the American Chemical Society |
| container_volume | 127 |
| creator | Shinohara, Toshio Deng, Hongbo Snapper, Marc L Hoveyda, Amir H |
| description | A Pd-mediated method for preparation of the strained macrocyclic moiety of complestatins is disclosed. Through stereoselective synthesis of model macrocycles and the S atropisomer of complestatin, the stereochemical identity of the anti-HIV agent complestatin is established. Investigations described herein illustrate that the compound previously reported as isocomplestatin is the same as complestatin. Thus, the S atropisomer of complestatin is the true isocomplestatin and has not been isolated as a natural product. |
| doi_str_mv | 10.1021/ja051790l |
| format | Article |
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Through stereoselective synthesis of model macrocycles and the S atropisomer of complestatin, the stereochemical identity of the anti-HIV agent complestatin is established. Investigations described herein illustrate that the compound previously reported as isocomplestatin is the same as complestatin. Thus, the S atropisomer of complestatin is the true isocomplestatin and has not been isolated as a natural product.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja051790l</identifier><identifier>PMID: 15898781</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral agents ; Biological and medical sciences ; Chemistry ; Chlorophenols - chemical synthesis ; Chlorophenols - chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms ; Medical sciences ; Molecular Conformation ; Oligopeptides - chemistry ; Organic chemistry ; Peptides, Cyclic - chemical synthesis ; Peptides, Cyclic - chemistry ; Pharmacology. 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Am. Chem. Soc</addtitle><description>A Pd-mediated method for preparation of the strained macrocyclic moiety of complestatins is disclosed. Through stereoselective synthesis of model macrocycles and the S atropisomer of complestatin, the stereochemical identity of the anti-HIV agent complestatin is established. Investigations described herein illustrate that the compound previously reported as isocomplestatin is the same as complestatin. Thus, the S atropisomer of complestatin is the true isocomplestatin and has not been isolated as a natural product.</description><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiviral agents</subject><subject>Biological and medical sciences</subject><subject>Chemistry</subject><subject>Chlorophenols - chemical synthesis</subject><subject>Chlorophenols - chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Medical sciences</subject><subject>Molecular Conformation</subject><subject>Oligopeptides - chemistry</subject><subject>Organic chemistry</subject><subject>Peptides, Cyclic - chemical synthesis</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Pharmacology. Drug treatments</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><subject>Streptomyces - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkL9OwzAYxC0EoqUw8AKoC0gMAduxY4cFoQpKUfkjUjqwWG7iCJckLnaC6MbKa_IkuGrVLkyfPt1Pp7sD4BDBMwQxOp9KSBGLYbEF2ohiGFCEo23QhhDigPEobIE956b-JZijXdBClMeccdQGlwNnUlPOCuVqWevq4vf7pzsytSy6ybyq35TTriurrJvUyiqTvqlSp158Vp_aaVPtg51cFk4drG4HvNxcj3q3wfCxP-hdDQNJCKsDyRVDMCaUownEKaQ0UxnDiONcQcJ5TlmWsSikYQYRjxkhea5kRCIcx4hzEnbAydJ3Zs1H48OKUrtUFYWslGmciBgnkNAFeLoEU2ucsyoXM6tLaecCQbFYS6zX8uzRyrSZlCrbkKt5PHC8AqTzrXMrq1S7DRfx0JeKPBcsOe1q9bXWpX33wUJGxegpEa_J_fihfzcWdOMrUyemprGV3-6fgH87wIxj</recordid><startdate>20050525</startdate><enddate>20050525</enddate><creator>Shinohara, Toshio</creator><creator>Deng, Hongbo</creator><creator>Snapper, Marc L</creator><creator>Hoveyda, Amir H</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050525</creationdate><title>Isocomplestatin: Total Synthesis and Stereochemical Revision</title><author>Shinohara, Toshio ; Deng, Hongbo ; Snapper, Marc L ; Hoveyda, Amir H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-a8e71094581b02c055ded72182fe0488f57dd76353d0189744ffea64629918843</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antiviral agents</topic><topic>Biological and medical sciences</topic><topic>Chemistry</topic><topic>Chlorophenols - chemical synthesis</topic><topic>Chlorophenols - chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Medical sciences</topic><topic>Molecular Conformation</topic><topic>Oligopeptides - chemistry</topic><topic>Organic chemistry</topic><topic>Peptides, Cyclic - chemical synthesis</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Pharmacology. Drug treatments</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><topic>Streptomyces - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shinohara, Toshio</creatorcontrib><creatorcontrib>Deng, Hongbo</creatorcontrib><creatorcontrib>Snapper, Marc L</creatorcontrib><creatorcontrib>Hoveyda, Amir H</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 the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shinohara, Toshio</au><au>Deng, Hongbo</au><au>Snapper, Marc L</au><au>Hoveyda, Amir H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isocomplestatin: Total Synthesis and Stereochemical Revision</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2005-05-25</date><risdate>2005</risdate><volume>127</volume><issue>20</issue><spage>7334</spage><epage>7336</epage><pages>7334-7336</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>A Pd-mediated method for preparation of the strained macrocyclic moiety of complestatins is disclosed. Through stereoselective synthesis of model macrocycles and the S atropisomer of complestatin, the stereochemical identity of the anti-HIV agent complestatin is established. Investigations described herein illustrate that the compound previously reported as isocomplestatin is the same as complestatin. Thus, the S atropisomer of complestatin is the true isocomplestatin and has not been isolated as a natural product.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15898781</pmid><doi>10.1021/ja051790l</doi><tpages>3</tpages></addata></record> |
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| subjects | Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Biological and medical sciences Chemistry Chlorophenols - chemical synthesis Chlorophenols - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Medical sciences Molecular Conformation Oligopeptides - chemistry Organic chemistry Peptides, Cyclic - chemical synthesis Peptides, Cyclic - chemistry Pharmacology. Drug treatments Preparations and properties Stereoisomerism Streptomyces - chemistry |
| title | Isocomplestatin: Total Synthesis and Stereochemical Revision |
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