First enantioselective synthesis of isagarin, a natural product isolated from Pentas longiflora Oliv
For the first time, an enantioselective synthesis of both 1 R,4 S-isagarin 1a and 1 S,4 R-isagarin 1b was achieved starting from 1,4-dimethoxy-2-vinylnaphthalene 2. The key steps involve a Sharpless asymmetric dihydroxylation and reaction with an acetonylating pyridinium ylid. The different optical...
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| Veröffentlicht in: | Tetrahedron 2010-07, Vol.66 (27), p.5158-5160 |
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| container_title | Tetrahedron |
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| creator | Jacobs, Jan Claessens, Sven De Mol, Eva El Hady, Samir Minguillón, Cristina Álvarez, Mercedes De Kimpe, Norbert |
| description | For the first time, an enantioselective synthesis of both 1
R,4
S-isagarin
1a and 1
S,4
R-isagarin
1b was achieved starting from 1,4-dimethoxy-2-vinylnaphthalene
2. The key steps involve a Sharpless asymmetric dihydroxylation and reaction with an acetonylating pyridinium ylid. The different optical rotations and melting points of the enantiopure 1
R,4
S-isagarin
1a and 1
S,4
R-isagarin
1b with respect to the isolated natural product will be addressed.
[Display omitted] |
| doi_str_mv | 10.1016/j.tet.2010.04.105 |
| format | Article |
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R,4
S-isagarin
1a and 1
S,4
R-isagarin
1b was achieved starting from 1,4-dimethoxy-2-vinylnaphthalene
2. The key steps involve a Sharpless asymmetric dihydroxylation and reaction with an acetonylating pyridinium ylid. The different optical rotations and melting points of the enantiopure 1
R,4
S-isagarin
1a and 1
S,4
R-isagarin
1b with respect to the isolated natural product will be addressed.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2010.04.105</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Asymmetric synthesis ; Isagarin ; Natural products ; Pentas longiflora Oliv ; Productes naturals ; Sharpless asymmetric dihydroxylation ; Síntesi asimètrica</subject><ispartof>Tetrahedron, 2010-07, Vol.66 (27), p.5158-5160</ispartof><rights>2010 Elsevier Ltd</rights><rights>(c) Elsevier B.V., 2010 info:eu-repo/semantics/openAccess</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c382t-e914af084cb3330f4c5740480a92a09709987535be389197efb876dc7493a9923</citedby><cites>FETCH-LOGICAL-c382t-e914af084cb3330f4c5740480a92a09709987535be389197efb876dc7493a9923</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0040402010006873$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,776,780,881,3536,26953,27903,27904,65309</link.rule.ids></links><search><creatorcontrib>Jacobs, Jan</creatorcontrib><creatorcontrib>Claessens, Sven</creatorcontrib><creatorcontrib>De Mol, Eva</creatorcontrib><creatorcontrib>El Hady, Samir</creatorcontrib><creatorcontrib>Minguillón, Cristina</creatorcontrib><creatorcontrib>Álvarez, Mercedes</creatorcontrib><creatorcontrib>De Kimpe, Norbert</creatorcontrib><title>First enantioselective synthesis of isagarin, a natural product isolated from Pentas longiflora Oliv</title><title>Tetrahedron</title><description>For the first time, an enantioselective synthesis of both 1
R,4
S-isagarin
1a and 1
S,4
R-isagarin
1b was achieved starting from 1,4-dimethoxy-2-vinylnaphthalene
2. The key steps involve a Sharpless asymmetric dihydroxylation and reaction with an acetonylating pyridinium ylid. The different optical rotations and melting points of the enantiopure 1
R,4
S-isagarin
1a and 1
S,4
R-isagarin
1b with respect to the isolated natural product will be addressed.
[Display omitted]</description><subject>Asymmetric synthesis</subject><subject>Isagarin</subject><subject>Natural products</subject><subject>Pentas longiflora Oliv</subject><subject>Productes naturals</subject><subject>Sharpless asymmetric dihydroxylation</subject><subject>Síntesi asimètrica</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>XX2</sourceid><recordid>eNp9kM9KAzEQxoMoWKsP4C0P4NbJn-1u8CTFqlDQg57DNDurKetGkrTQtzdFQU8ehmG-4Tcf8zF2KWAmQMyvN7NMeSahzKCLVB-xidBzXdVazI_ZBEBDpUHCKTtLaQMAQkg1Yd3Sx5Q5jThmHxIN5LLfEU_7Mb9T8omHnvuEbxj9eMWRj5i3EQf-GUO3dbnswoCZOt7H8MGfacyY-BDGN98PISJ_GvzunJ30OCS6-OlT9rq8e1k8VKun-8fF7apyqpW5IiM09tBqt1ZKQa9d3WjQLaCRCKYBY9qmVvWaVGuEaahft828c402Co2RasrE912Xts5GchQdZhvQ_w6HktBIK4tFq_8wMaQUqbef0X9g3FsB9hCt3dgSrT1Ea0EXqS7MzTdD5Zmdp2iT8zQ66nzxybYL_h_6C5VIggM</recordid><startdate>20100703</startdate><enddate>20100703</enddate><creator>Jacobs, Jan</creator><creator>Claessens, Sven</creator><creator>De Mol, Eva</creator><creator>El Hady, Samir</creator><creator>Minguillón, Cristina</creator><creator>Álvarez, Mercedes</creator><creator>De Kimpe, Norbert</creator><general>Elsevier Ltd</general><general>Elsevier B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>XX2</scope></search><sort><creationdate>20100703</creationdate><title>First enantioselective synthesis of isagarin, a natural product isolated from Pentas longiflora Oliv</title><author>Jacobs, Jan ; Claessens, Sven ; De Mol, Eva ; El Hady, Samir ; Minguillón, Cristina ; Álvarez, Mercedes ; De Kimpe, Norbert</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c382t-e914af084cb3330f4c5740480a92a09709987535be389197efb876dc7493a9923</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Asymmetric synthesis</topic><topic>Isagarin</topic><topic>Natural products</topic><topic>Pentas longiflora Oliv</topic><topic>Productes naturals</topic><topic>Sharpless asymmetric dihydroxylation</topic><topic>Síntesi asimètrica</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jacobs, Jan</creatorcontrib><creatorcontrib>Claessens, Sven</creatorcontrib><creatorcontrib>De Mol, Eva</creatorcontrib><creatorcontrib>El Hady, Samir</creatorcontrib><creatorcontrib>Minguillón, Cristina</creatorcontrib><creatorcontrib>Álvarez, Mercedes</creatorcontrib><creatorcontrib>De Kimpe, Norbert</creatorcontrib><collection>CrossRef</collection><collection>Recercat</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jacobs, Jan</au><au>Claessens, Sven</au><au>De Mol, Eva</au><au>El Hady, Samir</au><au>Minguillón, Cristina</au><au>Álvarez, Mercedes</au><au>De Kimpe, Norbert</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>First enantioselective synthesis of isagarin, a natural product isolated from Pentas longiflora Oliv</atitle><jtitle>Tetrahedron</jtitle><date>2010-07-03</date><risdate>2010</risdate><volume>66</volume><issue>27</issue><spage>5158</spage><epage>5160</epage><pages>5158-5160</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>For the first time, an enantioselective synthesis of both 1
R,4
S-isagarin
1a and 1
S,4
R-isagarin
1b was achieved starting from 1,4-dimethoxy-2-vinylnaphthalene
2. The key steps involve a Sharpless asymmetric dihydroxylation and reaction with an acetonylating pyridinium ylid. The different optical rotations and melting points of the enantiopure 1
R,4
S-isagarin
1a and 1
S,4
R-isagarin
1b with respect to the isolated natural product will be addressed.
[Display omitted]</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tet.2010.04.105</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Tetrahedron, 2010-07, Vol.66 (27), p.5158-5160 |
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| source | Elsevier ScienceDirect Journals; Recercat |
| subjects | Asymmetric synthesis Isagarin Natural products Pentas longiflora Oliv Productes naturals Sharpless asymmetric dihydroxylation Síntesi asimètrica |
| title | First enantioselective synthesis of isagarin, a natural product isolated from Pentas longiflora Oliv |
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