Formal Synthesis of (+)-Lasubine II and (−)-Subcosine II via Organocatalytic Michael Addition of a Ketone to an α‑Nitrostyrene
The first examples of an organocatalytic Michael addition of a ketone to in situ generated α-nitrostyrenes are reported. A suitably functionalized γ-nitroketone obtained from the organocatalyzed Michael addition was converted into (+)-2-epi-lasubine II, the immediate synthetic precursor of (+)-lasub...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2015-11, Vol.17 (21), p.5312-5315 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 5315 |
|---|---|
| container_issue | 21 |
| container_start_page | 5312 |
| container_title | Organic letters |
| container_volume | 17 |
| creator | N. V. G, Moorthy Dyapa, Rajendar Pansare, Sunil V |
| description | The first examples of an organocatalytic Michael addition of a ketone to in situ generated α-nitrostyrenes are reported. A suitably functionalized γ-nitroketone obtained from the organocatalyzed Michael addition was converted into (+)-2-epi-lasubine II, the immediate synthetic precursor of (+)-lasubine II and (−)-subcosine II (enantiomers of the natural quinolizidine alkaloids). Two of the three stereocenters in (+)-2-epi-lasubine II are set by the Michael reaction. |
| doi_str_mv | 10.1021/acs.orglett.5b02677 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1731783794</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1731783794</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-da307fd8f27c8b78743b0a153114ffd9825ecd188ff74a588c1bd830940bc3e93</originalsourceid><addsrcrecordid>eNp9kM9OGzEQxq2qqFDoEyAhH4OqTez1buw9IlQgIpRD6Hk16z-J0WZNbW-l3Cr1wrV9E16Eh-BJcJSFY08zGn3fNzM_hI4pGVOS0wnIMHZ-2eoYx2VD8innH9ABLXOWcVLmH9_7KdlHn0O4J4SmSfUJ7efTosqJmB6gPxfOr6HFi00XVzrYgJ3Bo6-n2RxC39hO49kMQ6fw6OXx32m26BvpwjD-ZQHf-iV0TkKEdhOtxDdWrkC3-EwpG63rtnGAr3V0yRNdisLPTy-__3630bsQN153-gjtGWiD_jLUQ_Tj4tvd-VU2v72cnZ_NM2BFGTMFjHCjhMm5FA0XvGANAVoySgtjVCXyUktFhTCGF1AKIWmjBCNVQRrJdMUO0WiX--Ddz16HWK9tkLptodOuDzXljHLBeFUkKdtJZboyeG3qB2_X4Dc1JfWWfp3o1wP9eqCfXCfDgr5Za_XuecOdBJOdYOu-d73v0r__jXwFxkWV5Q</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1731783794</pqid></control><display><type>article</type><title>Formal Synthesis of (+)-Lasubine II and (−)-Subcosine II via Organocatalytic Michael Addition of a Ketone to an α‑Nitrostyrene</title><source>ACS Publications</source><source>MEDLINE</source><creator>N. V. G, Moorthy ; Dyapa, Rajendar ; Pansare, Sunil V</creator><creatorcontrib>N. V. G, Moorthy ; Dyapa, Rajendar ; Pansare, Sunil V</creatorcontrib><description>The first examples of an organocatalytic Michael addition of a ketone to in situ generated α-nitrostyrenes are reported. A suitably functionalized γ-nitroketone obtained from the organocatalyzed Michael addition was converted into (+)-2-epi-lasubine II, the immediate synthetic precursor of (+)-lasubine II and (−)-subcosine II (enantiomers of the natural quinolizidine alkaloids). Two of the three stereocenters in (+)-2-epi-lasubine II are set by the Michael reaction.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.5b02677</identifier><identifier>PMID: 26492086</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkaloids - chemical synthesis ; Alkaloids - chemistry ; Ketones - chemistry ; Molecular Structure ; Nitro Compounds - chemistry ; Piperidines - chemistry ; Quinolizidines - chemical synthesis ; Quinolizidines - chemistry ; Quinolizines - chemical synthesis ; Quinolizines - chemistry ; Stereoisomerism ; Styrenes - chemistry</subject><ispartof>Organic letters, 2015-11, Vol.17 (21), p.5312-5315</ispartof><rights>Copyright © 2015 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-da307fd8f27c8b78743b0a153114ffd9825ecd188ff74a588c1bd830940bc3e93</citedby><cites>FETCH-LOGICAL-a345t-da307fd8f27c8b78743b0a153114ffd9825ecd188ff74a588c1bd830940bc3e93</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/acs.orglett.5b02677$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.5b02677$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26492086$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>N. V. G, Moorthy</creatorcontrib><creatorcontrib>Dyapa, Rajendar</creatorcontrib><creatorcontrib>Pansare, Sunil V</creatorcontrib><title>Formal Synthesis of (+)-Lasubine II and (−)-Subcosine II via Organocatalytic Michael Addition of a Ketone to an α‑Nitrostyrene</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The first examples of an organocatalytic Michael addition of a ketone to in situ generated α-nitrostyrenes are reported. A suitably functionalized γ-nitroketone obtained from the organocatalyzed Michael addition was converted into (+)-2-epi-lasubine II, the immediate synthetic precursor of (+)-lasubine II and (−)-subcosine II (enantiomers of the natural quinolizidine alkaloids). Two of the three stereocenters in (+)-2-epi-lasubine II are set by the Michael reaction.</description><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - chemistry</subject><subject>Ketones - chemistry</subject><subject>Molecular Structure</subject><subject>Nitro Compounds - chemistry</subject><subject>Piperidines - chemistry</subject><subject>Quinolizidines - chemical synthesis</subject><subject>Quinolizidines - chemistry</subject><subject>Quinolizines - chemical synthesis</subject><subject>Quinolizines - chemistry</subject><subject>Stereoisomerism</subject><subject>Styrenes - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kM9OGzEQxq2qqFDoEyAhH4OqTez1buw9IlQgIpRD6Hk16z-J0WZNbW-l3Cr1wrV9E16Eh-BJcJSFY08zGn3fNzM_hI4pGVOS0wnIMHZ-2eoYx2VD8innH9ABLXOWcVLmH9_7KdlHn0O4J4SmSfUJ7efTosqJmB6gPxfOr6HFi00XVzrYgJ3Bo6-n2RxC39hO49kMQ6fw6OXx32m26BvpwjD-ZQHf-iV0TkKEdhOtxDdWrkC3-EwpG63rtnGAr3V0yRNdisLPTy-__3630bsQN153-gjtGWiD_jLUQ_Tj4tvd-VU2v72cnZ_NM2BFGTMFjHCjhMm5FA0XvGANAVoySgtjVCXyUktFhTCGF1AKIWmjBCNVQRrJdMUO0WiX--Ddz16HWK9tkLptodOuDzXljHLBeFUkKdtJZboyeG3qB2_X4Dc1JfWWfp3o1wP9eqCfXCfDgr5Za_XuecOdBJOdYOu-d73v0r__jXwFxkWV5Q</recordid><startdate>20151106</startdate><enddate>20151106</enddate><creator>N. V. G, Moorthy</creator><creator>Dyapa, Rajendar</creator><creator>Pansare, Sunil V</creator><general>American Chemical Society</general><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>20151106</creationdate><title>Formal Synthesis of (+)-Lasubine II and (−)-Subcosine II via Organocatalytic Michael Addition of a Ketone to an α‑Nitrostyrene</title><author>N. V. G, Moorthy ; Dyapa, Rajendar ; Pansare, Sunil V</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-da307fd8f27c8b78743b0a153114ffd9825ecd188ff74a588c1bd830940bc3e93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Alkaloids - chemical synthesis</topic><topic>Alkaloids - chemistry</topic><topic>Ketones - chemistry</topic><topic>Molecular Structure</topic><topic>Nitro Compounds - chemistry</topic><topic>Piperidines - chemistry</topic><topic>Quinolizidines - chemical synthesis</topic><topic>Quinolizidines - chemistry</topic><topic>Quinolizines - chemical synthesis</topic><topic>Quinolizines - chemistry</topic><topic>Stereoisomerism</topic><topic>Styrenes - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>N. V. G, Moorthy</creatorcontrib><creatorcontrib>Dyapa, Rajendar</creatorcontrib><creatorcontrib>Pansare, Sunil V</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>N. V. G, Moorthy</au><au>Dyapa, Rajendar</au><au>Pansare, Sunil V</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Formal Synthesis of (+)-Lasubine II and (−)-Subcosine II via Organocatalytic Michael Addition of a Ketone to an α‑Nitrostyrene</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2015-11-06</date><risdate>2015</risdate><volume>17</volume><issue>21</issue><spage>5312</spage><epage>5315</epage><pages>5312-5315</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The first examples of an organocatalytic Michael addition of a ketone to in situ generated α-nitrostyrenes are reported. A suitably functionalized γ-nitroketone obtained from the organocatalyzed Michael addition was converted into (+)-2-epi-lasubine II, the immediate synthetic precursor of (+)-lasubine II and (−)-subcosine II (enantiomers of the natural quinolizidine alkaloids). Two of the three stereocenters in (+)-2-epi-lasubine II are set by the Michael reaction.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26492086</pmid><doi>10.1021/acs.orglett.5b02677</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2015-11, Vol.17 (21), p.5312-5315 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1731783794 |
| source | ACS Publications; MEDLINE |
| subjects | Alkaloids - chemical synthesis Alkaloids - chemistry Ketones - chemistry Molecular Structure Nitro Compounds - chemistry Piperidines - chemistry Quinolizidines - chemical synthesis Quinolizidines - chemistry Quinolizines - chemical synthesis Quinolizines - chemistry Stereoisomerism Styrenes - chemistry |
| title | Formal Synthesis of (+)-Lasubine II and (−)-Subcosine II via Organocatalytic Michael Addition of a Ketone to an α‑Nitrostyrene |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-10T22%3A41%3A44IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Formal%20Synthesis%20of%20(+)-Lasubine%20II%20and%20(%E2%88%92)-Subcosine%20II%20via%20Organocatalytic%20Michael%20Addition%20of%20a%20Ketone%20to%20an%20%CE%B1%E2%80%91Nitrostyrene&rft.jtitle=Organic%20letters&rft.au=N.%20V.%20G,%20Moorthy&rft.date=2015-11-06&rft.volume=17&rft.issue=21&rft.spage=5312&rft.epage=5315&rft.pages=5312-5315&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.5b02677&rft_dat=%3Cproquest_cross%3E1731783794%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1731783794&rft_id=info:pmid/26492086&rfr_iscdi=true |