Catalytic, Asymmetric Synthesis of Siphonarienal
This paper describes the synthesis of the marine natural product, siphonarienal. The key step of this synthesis is an aldol reaction that constructs most of the skeleton and sets all three stereocenters of the target in one step from commercially available starting materials. Deoxygenation and chain...
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Veröffentlicht in: | Journal of organic chemistry 2001-11, Vol.66 (22), p.7500-7504 |
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creator | Calter, Michael A Liao, Wensheng Struss, John A |
description | This paper describes the synthesis of the marine natural product, siphonarienal. The key step of this synthesis is an aldol reaction that constructs most of the skeleton and sets all three stereocenters of the target in one step from commercially available starting materials. Deoxygenation and chain homologation steps complete the synthesis. |
doi_str_mv | 10.1021/jo0160367 |
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The key step of this synthesis is an aldol reaction that constructs most of the skeleton and sets all three stereocenters of the target in one step from commercially available starting materials. Deoxygenation and chain homologation steps complete the synthesis.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo0160367</identifier><identifier>PMID: 11681967</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkanes - chemical synthesis ; Animals ; Anti-Infective Agents - chemistry ; Antineoplastic Agents - chemistry ; Biological Factors - chemical synthesis ; Biological Factors - chemistry ; Catalysis ; Molecular Structure ; Mollusca - chemistry ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2001-11, Vol.66 (22), p.7500-7504</ispartof><rights>Copyright © 2001 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a349t-232b3c6928c908142b2441e8c917b8faa7031e0dac0f759d5e4647d4fba7d6693</citedby><cites>FETCH-LOGICAL-a349t-232b3c6928c908142b2441e8c917b8faa7031e0dac0f759d5e4647d4fba7d6693</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo0160367$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo0160367$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27059,27907,27908,56721,56771</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11681967$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Calter, Michael A</creatorcontrib><creatorcontrib>Liao, Wensheng</creatorcontrib><creatorcontrib>Struss, John A</creatorcontrib><title>Catalytic, Asymmetric Synthesis of Siphonarienal</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>This paper describes the synthesis of the marine natural product, siphonarienal. The key step of this synthesis is an aldol reaction that constructs most of the skeleton and sets all three stereocenters of the target in one step from commercially available starting materials. Deoxygenation and chain homologation steps complete the synthesis.</description><subject>Alkanes - chemical synthesis</subject><subject>Animals</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Biological Factors - chemical synthesis</subject><subject>Biological Factors - chemistry</subject><subject>Catalysis</subject><subject>Molecular Structure</subject><subject>Mollusca - chemistry</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkF1LwzAUhoMobk4v_APSGwXBar6atJdj-D1w0InehTRNWWY_tqQF---NdMwbz83h8D68Bx4AzhG8RRCju3UDEYOE8QMwRhGGIUsgPQRjCDEOCWZkBE6cW0M_URQdgxFCLEYJ42MAZ7KVZd8adRNMXV9VurVGBWlftyvtjAuaIkjNZtXU0hpdy_IUHBWydPpstyfg_eF-OXsK52-Pz7PpPJSEJm2ICc6IYgmOVQJjRHGGKUXaX4hncSElhwRpmEsFCx4leaQpozynRSZ5zlhCJuBq6N3YZttp14rKOKXLUta66ZzgGBNOKfPg9QAq2zhndSE21lTS9gJB8atH7PV49mJX2mWVzv_InQ8PhANgXKu_97m0X8KnPBLLRSrIJ0k_6OJFvHr-cuClcv5PZ70h98_jHwUoePM</recordid><startdate>20011102</startdate><enddate>20011102</enddate><creator>Calter, Michael A</creator><creator>Liao, Wensheng</creator><creator>Struss, John A</creator><general>American Chemical Society</general><scope>BSCLL</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>20011102</creationdate><title>Catalytic, Asymmetric Synthesis of Siphonarienal</title><author>Calter, Michael A ; Liao, Wensheng ; Struss, John A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a349t-232b3c6928c908142b2441e8c917b8faa7031e0dac0f759d5e4647d4fba7d6693</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Alkanes - chemical synthesis</topic><topic>Animals</topic><topic>Anti-Infective Agents - chemistry</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Biological Factors - chemical synthesis</topic><topic>Biological Factors - chemistry</topic><topic>Catalysis</topic><topic>Molecular Structure</topic><topic>Mollusca - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Calter, Michael A</creatorcontrib><creatorcontrib>Liao, Wensheng</creatorcontrib><creatorcontrib>Struss, John A</creatorcontrib><collection>Istex</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>Calter, Michael A</au><au>Liao, Wensheng</au><au>Struss, John A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic, Asymmetric Synthesis of Siphonarienal</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2001-11-02</date><risdate>2001</risdate><volume>66</volume><issue>22</issue><spage>7500</spage><epage>7504</epage><pages>7500-7504</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>This paper describes the synthesis of the marine natural product, siphonarienal. The key step of this synthesis is an aldol reaction that constructs most of the skeleton and sets all three stereocenters of the target in one step from commercially available starting materials. Deoxygenation and chain homologation steps complete the synthesis.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>11681967</pmid><doi>10.1021/jo0160367</doi><tpages>5</tpages></addata></record> |
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subjects | Alkanes - chemical synthesis Animals Anti-Infective Agents - chemistry Antineoplastic Agents - chemistry Biological Factors - chemical synthesis Biological Factors - chemistry Catalysis Molecular Structure Mollusca - chemistry Stereoisomerism |
title | Catalytic, Asymmetric Synthesis of Siphonarienal |
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