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Asymmetric synthesis of N,O-diacetyl-3-epi-xestoaminol C: structure and absolute configuration confirmation of 3-epi-xestoaminol C
[Display omitted] The asymmetric synthesis of N,O-diacetyl-3-epi-xestoaminol C is reported. The synthesis employs diastereoselective aminohydroxylation of tert-butyl crotonate [conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide, then in situ enolate oxidation with (+)-camphorsulfonyl...
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| Published in: | Tetrahedron letters 2016-03, Vol.57 (11), p.1270-1272 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c409t-2402b1043f3fa379a76f284b389b20ede1bc066f4353490a396a1f682ecb98623 |
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| cites | cdi_FETCH-LOGICAL-c409t-2402b1043f3fa379a76f284b389b20ede1bc066f4353490a396a1f682ecb98623 |
| container_end_page | 1272 |
| container_issue | 11 |
| container_start_page | 1270 |
| container_title | Tetrahedron letters |
| container_volume | 57 |
| creator | Archer, Susanna G. Csatayová, Kristína Davies, Stephen G. Fletcher, Ai M. Roberts, Paul M. Thomson, James E. |
| description | [Display omitted]
The asymmetric synthesis of N,O-diacetyl-3-epi-xestoaminol C is reported. The synthesis employs diastereoselective aminohydroxylation of tert-butyl crotonate [conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide, then in situ enolate oxidation with (+)-camphorsulfonyloxaziridine (CSO)] and a diastereoselective reduction protocol as the key stereodefining steps. The synthetic sample of the natural product was isolated as its N,O-diacetyl derivative for ease of purification; this material was prepared in ten steps and 17% overall yield from commercially available tert-butyl crotonate. This synthesis confirms unambiguously both the assigned structure and absolute (S,S)-configuration of the natural product. |
| doi_str_mv | 10.1016/j.tetlet.2016.02.021 |
| format | article |
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The asymmetric synthesis of N,O-diacetyl-3-epi-xestoaminol C is reported. The synthesis employs diastereoselective aminohydroxylation of tert-butyl crotonate [conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide, then in situ enolate oxidation with (+)-camphorsulfonyloxaziridine (CSO)] and a diastereoselective reduction protocol as the key stereodefining steps. The synthetic sample of the natural product was isolated as its N,O-diacetyl derivative for ease of purification; this material was prepared in ten steps and 17% overall yield from commercially available tert-butyl crotonate. This synthesis confirms unambiguously both the assigned structure and absolute (S,S)-configuration of the natural product.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2016.02.021</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>3-epi-Xestoaminol C ; Asymmetry ; Conjugate addition ; Conjugates ; Derivatives ; Lithium ; Natural product ; Natural products ; Purification ; Synthesis ; Tetrahedrons ; Xestoaminol C</subject><ispartof>Tetrahedron letters, 2016-03, Vol.57 (11), p.1270-1272</ispartof><rights>2016 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c409t-2402b1043f3fa379a76f284b389b20ede1bc066f4353490a396a1f682ecb98623</citedby><cites>FETCH-LOGICAL-c409t-2402b1043f3fa379a76f284b389b20ede1bc066f4353490a396a1f682ecb98623</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Archer, Susanna G.</creatorcontrib><creatorcontrib>Csatayová, Kristína</creatorcontrib><creatorcontrib>Davies, Stephen G.</creatorcontrib><creatorcontrib>Fletcher, Ai M.</creatorcontrib><creatorcontrib>Roberts, Paul M.</creatorcontrib><creatorcontrib>Thomson, James E.</creatorcontrib><title>Asymmetric synthesis of N,O-diacetyl-3-epi-xestoaminol C: structure and absolute configuration confirmation of 3-epi-xestoaminol C</title><title>Tetrahedron letters</title><description>[Display omitted]
The asymmetric synthesis of N,O-diacetyl-3-epi-xestoaminol C is reported. The synthesis employs diastereoselective aminohydroxylation of tert-butyl crotonate [conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide, then in situ enolate oxidation with (+)-camphorsulfonyloxaziridine (CSO)] and a diastereoselective reduction protocol as the key stereodefining steps. The synthetic sample of the natural product was isolated as its N,O-diacetyl derivative for ease of purification; this material was prepared in ten steps and 17% overall yield from commercially available tert-butyl crotonate. This synthesis confirms unambiguously both the assigned structure and absolute (S,S)-configuration of the natural product.</description><subject>3-epi-Xestoaminol C</subject><subject>Asymmetry</subject><subject>Conjugate addition</subject><subject>Conjugates</subject><subject>Derivatives</subject><subject>Lithium</subject><subject>Natural product</subject><subject>Natural products</subject><subject>Purification</subject><subject>Synthesis</subject><subject>Tetrahedrons</subject><subject>Xestoaminol C</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp9UMtqHDEQFCYGb-z8gQ9zzMFatx7WjnIwmMWJA4t9sc9Co2k5WmZGG0kTvNd8eWQmx5CmoCmoKrqLkEsGawZMXe_XBcuAZc0rWwOvYCdkxdqNoOKmZR_ICkAClSD0GfmY8x7qqBZW5PddPo4jlhRck49T-YE55Cb65vHqifbBOizHgQqKh0DfMJdoxzDFodl-aXJJsytzwsZOfWO7HIe5YOPi5MPrnGwJcVpYGhdSY_-RdEFOvR0yfvq7z8nL1_vn7QPdPX37vr3bUSdBF8ol8I6BFF54KzbabpTnrexEqzsO2CPrHCjlpbgRUoMVWlnmVcvRdbpVXJyTz0vuIcWfc73AjCE7HAY7YZyzYS1oJYQWqkrlInUp5pzQm0MKo01Hw8C8V272ZqncvFdugFewartdbFjf-BUwmewCTg77kNAV08fw_4A_Cf-NqQ</recordid><startdate>20160316</startdate><enddate>20160316</enddate><creator>Archer, Susanna G.</creator><creator>Csatayová, Kristína</creator><creator>Davies, Stephen G.</creator><creator>Fletcher, Ai M.</creator><creator>Roberts, Paul M.</creator><creator>Thomson, James E.</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20160316</creationdate><title>Asymmetric synthesis of N,O-diacetyl-3-epi-xestoaminol C: structure and absolute configuration confirmation of 3-epi-xestoaminol C</title><author>Archer, Susanna G. ; Csatayová, Kristína ; Davies, Stephen G. ; Fletcher, Ai M. ; Roberts, Paul M. ; Thomson, James E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c409t-2402b1043f3fa379a76f284b389b20ede1bc066f4353490a396a1f682ecb98623</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>3-epi-Xestoaminol C</topic><topic>Asymmetry</topic><topic>Conjugate addition</topic><topic>Conjugates</topic><topic>Derivatives</topic><topic>Lithium</topic><topic>Natural product</topic><topic>Natural products</topic><topic>Purification</topic><topic>Synthesis</topic><topic>Tetrahedrons</topic><topic>Xestoaminol C</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Archer, Susanna G.</creatorcontrib><creatorcontrib>Csatayová, Kristína</creatorcontrib><creatorcontrib>Davies, Stephen G.</creatorcontrib><creatorcontrib>Fletcher, Ai M.</creatorcontrib><creatorcontrib>Roberts, Paul M.</creatorcontrib><creatorcontrib>Thomson, James E.</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Archer, Susanna G.</au><au>Csatayová, Kristína</au><au>Davies, Stephen G.</au><au>Fletcher, Ai M.</au><au>Roberts, Paul M.</au><au>Thomson, James E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric synthesis of N,O-diacetyl-3-epi-xestoaminol C: structure and absolute configuration confirmation of 3-epi-xestoaminol C</atitle><jtitle>Tetrahedron letters</jtitle><date>2016-03-16</date><risdate>2016</risdate><volume>57</volume><issue>11</issue><spage>1270</spage><epage>1272</epage><pages>1270-1272</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>[Display omitted]
The asymmetric synthesis of N,O-diacetyl-3-epi-xestoaminol C is reported. The synthesis employs diastereoselective aminohydroxylation of tert-butyl crotonate [conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide, then in situ enolate oxidation with (+)-camphorsulfonyloxaziridine (CSO)] and a diastereoselective reduction protocol as the key stereodefining steps. The synthetic sample of the natural product was isolated as its N,O-diacetyl derivative for ease of purification; this material was prepared in ten steps and 17% overall yield from commercially available tert-butyl crotonate. This synthesis confirms unambiguously both the assigned structure and absolute (S,S)-configuration of the natural product.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2016.02.021</doi><tpages>3</tpages></addata></record> |
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| ispartof | Tetrahedron letters, 2016-03, Vol.57 (11), p.1270-1272 |
| issn | 0040-4039 1873-3581 |
| language | eng |
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| source | Elsevier |
| subjects | 3-epi-Xestoaminol C Asymmetry Conjugate addition Conjugates Derivatives Lithium Natural product Natural products Purification Synthesis Tetrahedrons Xestoaminol C |
| title | Asymmetric synthesis of N,O-diacetyl-3-epi-xestoaminol C: structure and absolute configuration confirmation of 3-epi-xestoaminol C |
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