Total Synthesis of Borrelidin
The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11−C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated...
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| Veröffentlicht in: | Journal of organic chemistry 2007-04, Vol.72 (8), p.2744-2756 |
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| container_end_page | 2756 |
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| container_issue | 8 |
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| container_title | Journal of organic chemistry |
| container_volume | 72 |
| creator | Nagamitsu, Tohru Takano, Daisuke Marumoto, Kaori Fukuda, Takeo Furuya, Kentaro Otoguro, Kazuhiko Takeda, Kazuyoshi Kuwajima, Isao Harigaya, Yoshihiro Ōmura, Satoshi |
| description | The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11−C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated intramolecular Reformatsky-type reaction as the most efficient synthetic approach. The two key segments were synthesized through regioselective methylation, directed hydrogenation, stereoselective Reformatsky-type reaction, and MgBr2·Et2O-mediated chelation-controlled allylation. |
| doi_str_mv | 10.1021/jo062089i |
| format | Article |
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The best feature of our synthetic route is macrocyclization at C11−C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated intramolecular Reformatsky-type reaction as the most efficient synthetic approach. 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Org. Chem</addtitle><description>The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11−C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated intramolecular Reformatsky-type reaction as the most efficient synthetic approach. The two key segments were synthesized through regioselective methylation, directed hydrogenation, stereoselective Reformatsky-type reaction, and MgBr2·Et2O-mediated chelation-controlled allylation.</description><subject>Chemistry</subject><subject>Cyclization</subject><subject>Exact sciences and technology</subject><subject>Fatty Alcohols - chemical synthesis</subject><subject>Fatty Alcohols - chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1LwzAcBvAgipvTgx9A2UXBQ_WfpkmaoxtuCr7hJngLaZpiZtfOpAX37Y2sbBdzySE_Hp48CJ1iuMYQ45tFDSyGVNg91Mc0hogJSPZRHyCOIxIz0kNH3i8gHErpIephTijFSdpHZ_O6UeVwtq6aT-OtH9bFcFQ7Z0qb2-oYHRSq9OakuwfofXI3H99Hjy_Th_HtY6QSzJooEyw1BVMKTM6LBHCaskInOEmyhBMtCsNEhlPFiNCQgWLBU5UTjgGT0JcM0OUmd-Xq79b4Ri6t16YsVWXq1ksOhAkhaIBXG6hd7b0zhVw5u1RuLTHIvy3kdotgz7vQNluafCe7zwdw0QHltSoLpypt_c6lTFBI4-CijbO-MT_bd-W-JOOEUzl_ncnRx9Pb5HnKJd_lKu1Dn9ZVYbt_Cv4Ck6Z-1g</recordid><startdate>20070413</startdate><enddate>20070413</enddate><creator>Nagamitsu, Tohru</creator><creator>Takano, Daisuke</creator><creator>Marumoto, Kaori</creator><creator>Fukuda, Takeo</creator><creator>Furuya, Kentaro</creator><creator>Otoguro, Kazuhiko</creator><creator>Takeda, Kazuyoshi</creator><creator>Kuwajima, Isao</creator><creator>Harigaya, Yoshihiro</creator><creator>Ōmura, Satoshi</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>20070413</creationdate><title>Total Synthesis of Borrelidin</title><author>Nagamitsu, Tohru ; Takano, Daisuke ; Marumoto, Kaori ; Fukuda, Takeo ; Furuya, Kentaro ; Otoguro, Kazuhiko ; Takeda, Kazuyoshi ; Kuwajima, Isao ; Harigaya, Yoshihiro ; Ōmura, Satoshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a416t-b968ef6aa0ed7f401886fc4144b473c9fe69b18a639c0b0a69685ad3710135203</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Chemistry</topic><topic>Cyclization</topic><topic>Exact sciences and technology</topic><topic>Fatty Alcohols - chemical synthesis</topic><topic>Fatty Alcohols - chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nagamitsu, Tohru</creatorcontrib><creatorcontrib>Takano, Daisuke</creatorcontrib><creatorcontrib>Marumoto, Kaori</creatorcontrib><creatorcontrib>Fukuda, Takeo</creatorcontrib><creatorcontrib>Furuya, Kentaro</creatorcontrib><creatorcontrib>Otoguro, Kazuhiko</creatorcontrib><creatorcontrib>Takeda, Kazuyoshi</creatorcontrib><creatorcontrib>Kuwajima, Isao</creatorcontrib><creatorcontrib>Harigaya, Yoshihiro</creatorcontrib><creatorcontrib>Ōmura, Satoshi</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>Nagamitsu, Tohru</au><au>Takano, Daisuke</au><au>Marumoto, Kaori</au><au>Fukuda, Takeo</au><au>Furuya, Kentaro</au><au>Otoguro, Kazuhiko</au><au>Takeda, Kazuyoshi</au><au>Kuwajima, Isao</au><au>Harigaya, Yoshihiro</au><au>Ōmura, Satoshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of Borrelidin</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. 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| subjects | Chemistry Cyclization Exact sciences and technology Fatty Alcohols - chemical synthesis Fatty Alcohols - chemistry Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Molecular Structure Organic chemistry Preparations and properties Stereoisomerism |
| title | Total Synthesis of Borrelidin |
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