A short synthesis of both enantiomers of 2-aminobicyclo[3.2.0]heptane-2,7-dicarboxylic acid
[Display omitted] •Photochemical access to a functionalized bicyclo[3.2.0]heptane skeleton.•Preparation of a constrained analogue of glutamic acid.•Use of an oxazolidinone for chiral resolution of an amino acid.•High stereoselectivity in a Bucherer-Bergs reaction. A concise method is reported for th...
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| Veröffentlicht in: | Tetrahedron letters 2021-03, Vol.68, p.152912, Article 152912 |
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| creator | Charnay-Pouget, Florence Le Liepvre, Matthieu Eijsberg, Hendrik Guillot, Régis Ollivier, Jean Secci, Francesco Frongia, Angelo Aitken, David J. |
| description | [Display omitted]
•Photochemical access to a functionalized bicyclo[3.2.0]heptane skeleton.•Preparation of a constrained analogue of glutamic acid.•Use of an oxazolidinone for chiral resolution of an amino acid.•High stereoselectivity in a Bucherer-Bergs reaction.
A concise method is reported for the synthesis of 2-aminobicyclo[3.2.0]heptane-2,7-dicarboxylic acid, a close analogue of the glutamate receptor ligand LY354740, in both enantiomeric forms. The strategy features the creation of the core structure at the start of the synthesis via a photochemical [2 + 2] cycloaddition reaction, an efficient resolution procedure using a chiral oxazolidinone, and requires only minimal purification of the synthetic intermediates. The title compounds showed little or no affinity for the mGlu2 and mGlu3 receptors. |
| doi_str_mv | 10.1016/j.tetlet.2021.152912 |
| format | Article |
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•Photochemical access to a functionalized bicyclo[3.2.0]heptane skeleton.•Preparation of a constrained analogue of glutamic acid.•Use of an oxazolidinone for chiral resolution of an amino acid.•High stereoselectivity in a Bucherer-Bergs reaction.
A concise method is reported for the synthesis of 2-aminobicyclo[3.2.0]heptane-2,7-dicarboxylic acid, a close analogue of the glutamate receptor ligand LY354740, in both enantiomeric forms. The strategy features the creation of the core structure at the start of the synthesis via a photochemical [2 + 2] cycloaddition reaction, an efficient resolution procedure using a chiral oxazolidinone, and requires only minimal purification of the synthetic intermediates. The title compounds showed little or no affinity for the mGlu2 and mGlu3 receptors.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2021.152912</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Bicyclo[3.2.0]heptane derivatives ; Chemical Sciences ; Glutamic acid analog ; Life Sciences ; Physics ; Resolution procedure ; Synthetic photochemistry</subject><ispartof>Tetrahedron letters, 2021-03, Vol.68, p.152912, Article 152912</ispartof><rights>2021 Elsevier Ltd</rights><rights>Attribution - NonCommercial</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c386t-19985250b2dc544ab0ed856d431db531e2087ef625e4e34926ff6a8f1a0990a33</citedby><cites>FETCH-LOGICAL-c386t-19985250b2dc544ab0ed856d431db531e2087ef625e4e34926ff6a8f1a0990a33</cites><orcidid>0000-0002-3540-9573 ; 0000-0002-5164-6042</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tetlet.2021.152912$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://hal.science/hal-03917652$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Charnay-Pouget, Florence</creatorcontrib><creatorcontrib>Le Liepvre, Matthieu</creatorcontrib><creatorcontrib>Eijsberg, Hendrik</creatorcontrib><creatorcontrib>Guillot, Régis</creatorcontrib><creatorcontrib>Ollivier, Jean</creatorcontrib><creatorcontrib>Secci, Francesco</creatorcontrib><creatorcontrib>Frongia, Angelo</creatorcontrib><creatorcontrib>Aitken, David J.</creatorcontrib><title>A short synthesis of both enantiomers of 2-aminobicyclo[3.2.0]heptane-2,7-dicarboxylic acid</title><title>Tetrahedron letters</title><description>[Display omitted]
•Photochemical access to a functionalized bicyclo[3.2.0]heptane skeleton.•Preparation of a constrained analogue of glutamic acid.•Use of an oxazolidinone for chiral resolution of an amino acid.•High stereoselectivity in a Bucherer-Bergs reaction.
A concise method is reported for the synthesis of 2-aminobicyclo[3.2.0]heptane-2,7-dicarboxylic acid, a close analogue of the glutamate receptor ligand LY354740, in both enantiomeric forms. The strategy features the creation of the core structure at the start of the synthesis via a photochemical [2 + 2] cycloaddition reaction, an efficient resolution procedure using a chiral oxazolidinone, and requires only minimal purification of the synthetic intermediates. The title compounds showed little or no affinity for the mGlu2 and mGlu3 receptors.</description><subject>Bicyclo[3.2.0]heptane derivatives</subject><subject>Chemical Sciences</subject><subject>Glutamic acid analog</subject><subject>Life Sciences</subject><subject>Physics</subject><subject>Resolution procedure</subject><subject>Synthetic photochemistry</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kF9LwzAUxYMoOKffwIe-CqbmT5OmL8IY6oSBL_o0JKTpLc3ompGE4b69nRUfvS8XDuccOD-EbinJKaHyYZsnSD2knBFGcypYRdkZmlFVcsyFoudoRkhBcEF4dYmuYtyS8aQiM7RZZLHzIWXxOKQOoouZb7Papy6DwQzJ-R2EH41hs3ODr5092t5veM5y8tnBPpkBMLsvceOsCbX_OvbOZsa65hpdtKaPcPP75-jj-el9ucLrt5fX5WKNLVcyYVpVSjBBatZYURSmJtAoIZuC06YWnAIjqoRWMgEF8KJism2lUS01pKqI4XyO7qbezvR6H9zOhKP2xunVYq1P2jibllKwAx29xeS1wccYoP0LUKJPMPVWTzD1CaaeYI6xxykG446Dg6CjdTBYaFwAm3Tj3f8F31XffbE</recordid><startdate>20210330</startdate><enddate>20210330</enddate><creator>Charnay-Pouget, Florence</creator><creator>Le Liepvre, Matthieu</creator><creator>Eijsberg, Hendrik</creator><creator>Guillot, Régis</creator><creator>Ollivier, Jean</creator><creator>Secci, Francesco</creator><creator>Frongia, Angelo</creator><creator>Aitken, David J.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-3540-9573</orcidid><orcidid>https://orcid.org/0000-0002-5164-6042</orcidid></search><sort><creationdate>20210330</creationdate><title>A short synthesis of both enantiomers of 2-aminobicyclo[3.2.0]heptane-2,7-dicarboxylic acid</title><author>Charnay-Pouget, Florence ; Le Liepvre, Matthieu ; Eijsberg, Hendrik ; Guillot, Régis ; Ollivier, Jean ; Secci, Francesco ; Frongia, Angelo ; Aitken, David J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c386t-19985250b2dc544ab0ed856d431db531e2087ef625e4e34926ff6a8f1a0990a33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Bicyclo[3.2.0]heptane derivatives</topic><topic>Chemical Sciences</topic><topic>Glutamic acid analog</topic><topic>Life Sciences</topic><topic>Physics</topic><topic>Resolution procedure</topic><topic>Synthetic photochemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Charnay-Pouget, Florence</creatorcontrib><creatorcontrib>Le Liepvre, Matthieu</creatorcontrib><creatorcontrib>Eijsberg, Hendrik</creatorcontrib><creatorcontrib>Guillot, Régis</creatorcontrib><creatorcontrib>Ollivier, Jean</creatorcontrib><creatorcontrib>Secci, Francesco</creatorcontrib><creatorcontrib>Frongia, Angelo</creatorcontrib><creatorcontrib>Aitken, David J.</creatorcontrib><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Charnay-Pouget, Florence</au><au>Le Liepvre, Matthieu</au><au>Eijsberg, Hendrik</au><au>Guillot, Régis</au><au>Ollivier, Jean</au><au>Secci, Francesco</au><au>Frongia, Angelo</au><au>Aitken, David J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A short synthesis of both enantiomers of 2-aminobicyclo[3.2.0]heptane-2,7-dicarboxylic acid</atitle><jtitle>Tetrahedron letters</jtitle><date>2021-03-30</date><risdate>2021</risdate><volume>68</volume><spage>152912</spage><pages>152912-</pages><artnum>152912</artnum><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>[Display omitted]
•Photochemical access to a functionalized bicyclo[3.2.0]heptane skeleton.•Preparation of a constrained analogue of glutamic acid.•Use of an oxazolidinone for chiral resolution of an amino acid.•High stereoselectivity in a Bucherer-Bergs reaction.
A concise method is reported for the synthesis of 2-aminobicyclo[3.2.0]heptane-2,7-dicarboxylic acid, a close analogue of the glutamate receptor ligand LY354740, in both enantiomeric forms. The strategy features the creation of the core structure at the start of the synthesis via a photochemical [2 + 2] cycloaddition reaction, an efficient resolution procedure using a chiral oxazolidinone, and requires only minimal purification of the synthetic intermediates. The title compounds showed little or no affinity for the mGlu2 and mGlu3 receptors.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2021.152912</doi><orcidid>https://orcid.org/0000-0002-3540-9573</orcidid><orcidid>https://orcid.org/0000-0002-5164-6042</orcidid><oa>free_for_read</oa></addata></record> |
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| language | eng |
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| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Bicyclo[3.2.0]heptane derivatives Chemical Sciences Glutamic acid analog Life Sciences Physics Resolution procedure Synthetic photochemistry |
| title | A short synthesis of both enantiomers of 2-aminobicyclo[3.2.0]heptane-2,7-dicarboxylic acid |
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