Recent advances in the total synthesis of polyhydroxylated alkaloids via chiral oxazines
This review summarizes recently established methodologies developed for the enantioselective and diastereoselective synthesis of chiral 1,3-oxazines. These compounds are of interest as advanced synthetic intermediates in the total synthesis of structurally complex and biologically active polyhydroxy...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2024-01, Vol.22 (5), p.894-926 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Park, Seokhwi Myeong, In-Soo Ham, Won-Hun |
| description | This review summarizes recently established methodologies developed for the enantioselective and diastereoselective synthesis of chiral 1,3-oxazines. These compounds are of interest as advanced synthetic intermediates in the total synthesis of structurally complex and biologically active polyhydroxylated alkaloids such as (+)-1-deoxynojirimycin, (-)-anisomycin, (+)-castanospermine, (+)-casuarine, (-)-conduramine F-1, (-)-sphingofungin B, Neu5Ac methyl ester, and other natural products. The devised synthetic approach aims to offer a direct, efficient, and adaptable method for obtaining both pure enantiomers and pure diastereomers. It revolves around utilizing chiral building blocks like
,
-,
,
,
-,
,
-,
,
,
-,
,
-,
,
,
-, and
,
,
-oxazines. By integrating oxazine chemistry with established and innovative transformations, this approach enabled the synthesis of 30 polyhydroxylated amines across various studies conducted between 2007 and 2022. |
| doi_str_mv | 10.1039/d3ob01624b |
| format | Article |
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,
-,
,
,
-,
,
-,
,
,
-,
,
-,
,
,
-, and
,
,
-oxazines. By integrating oxazine chemistry with established and innovative transformations, this approach enabled the synthesis of 30 polyhydroxylated amines across various studies conducted between 2007 and 2022.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d3ob01624b</identifier><identifier>PMID: 38230703</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkaloids ; Amines ; Anisomycin ; Biological activity ; Diastereoisomers ; Enantiomers ; Intermediates ; Natural products ; Oxazine ; Stereoselectivity ; Synthesis</subject><ispartof>Organic & biomolecular chemistry, 2024-01, Vol.22 (5), p.894-926</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c274t-eec15ae927892c32abcf137d65c3f352b31300cbb315e2be7ba3f5650b7cdea53</cites><orcidid>0000-0003-0085-2994 ; 0000-0001-8611-7776 ; 0000-0003-3982-5264</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38230703$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Park, Seokhwi</creatorcontrib><creatorcontrib>Myeong, In-Soo</creatorcontrib><creatorcontrib>Ham, Won-Hun</creatorcontrib><title>Recent advances in the total synthesis of polyhydroxylated alkaloids via chiral oxazines</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>This review summarizes recently established methodologies developed for the enantioselective and diastereoselective synthesis of chiral 1,3-oxazines. These compounds are of interest as advanced synthetic intermediates in the total synthesis of structurally complex and biologically active polyhydroxylated alkaloids such as (+)-1-deoxynojirimycin, (-)-anisomycin, (+)-castanospermine, (+)-casuarine, (-)-conduramine F-1, (-)-sphingofungin B, Neu5Ac methyl ester, and other natural products. The devised synthetic approach aims to offer a direct, efficient, and adaptable method for obtaining both pure enantiomers and pure diastereomers. It revolves around utilizing chiral building blocks like
,
-,
,
,
-,
,
-,
,
,
-,
,
-,
,
,
-, and
,
,
-oxazines. By integrating oxazine chemistry with established and innovative transformations, this approach enabled the synthesis of 30 polyhydroxylated amines across various studies conducted between 2007 and 2022.</description><subject>Alkaloids</subject><subject>Amines</subject><subject>Anisomycin</subject><subject>Biological activity</subject><subject>Diastereoisomers</subject><subject>Enantiomers</subject><subject>Intermediates</subject><subject>Natural products</subject><subject>Oxazine</subject><subject>Stereoselectivity</subject><subject>Synthesis</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpdkMtKw0AUhgdRbK1ufAAZcCNCdC6ZTGZp6xUKBVFwF-ZyQlPTTM0kpfHpjVa7cPWfA9_5OXwInVJyRQlX1457Q2jCYrOHhjSWMiKCq_3dzMgAHYWwIIQqmcSHaMBTxokkfIjensFC1WDt1rqyEHBR4WYOuPGNLnHoqn4JRcA-xytfdvPO1X7TlboBh3X5rktfuIDXhcZ2XtT9id_oz6KCcIwOcl0GOPnNEXq9v3uZPEbT2cPT5GYaWSbjJgKwVGhQTKaKWc60sTnl0iXC8pwLZjjlhFjTpwBmQBrNc5EIYqR1oAUfoYtt76r2Hy2EJlsWwUJZ6gp8GzKmqFCpVLHs0fN_6MK3ddV_11OMkFimQvXU5ZaytQ-hhjxb1cVS111GSfbtO7vls_GP73EPn_1WtmYJbof-CeZf0lN7qA</recordid><startdate>20240131</startdate><enddate>20240131</enddate><creator>Park, Seokhwi</creator><creator>Myeong, In-Soo</creator><creator>Ham, Won-Hun</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-0085-2994</orcidid><orcidid>https://orcid.org/0000-0001-8611-7776</orcidid><orcidid>https://orcid.org/0000-0003-3982-5264</orcidid></search><sort><creationdate>20240131</creationdate><title>Recent advances in the total synthesis of polyhydroxylated alkaloids via chiral oxazines</title><author>Park, Seokhwi ; Myeong, In-Soo ; Ham, Won-Hun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c274t-eec15ae927892c32abcf137d65c3f352b31300cbb315e2be7ba3f5650b7cdea53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Alkaloids</topic><topic>Amines</topic><topic>Anisomycin</topic><topic>Biological activity</topic><topic>Diastereoisomers</topic><topic>Enantiomers</topic><topic>Intermediates</topic><topic>Natural products</topic><topic>Oxazine</topic><topic>Stereoselectivity</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Park, Seokhwi</creatorcontrib><creatorcontrib>Myeong, In-Soo</creatorcontrib><creatorcontrib>Ham, Won-Hun</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Park, Seokhwi</au><au>Myeong, In-Soo</au><au>Ham, Won-Hun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Recent advances in the total synthesis of polyhydroxylated alkaloids via chiral oxazines</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2024-01-31</date><risdate>2024</risdate><volume>22</volume><issue>5</issue><spage>894</spage><epage>926</epage><pages>894-926</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>This review summarizes recently established methodologies developed for the enantioselective and diastereoselective synthesis of chiral 1,3-oxazines. These compounds are of interest as advanced synthetic intermediates in the total synthesis of structurally complex and biologically active polyhydroxylated alkaloids such as (+)-1-deoxynojirimycin, (-)-anisomycin, (+)-castanospermine, (+)-casuarine, (-)-conduramine F-1, (-)-sphingofungin B, Neu5Ac methyl ester, and other natural products. The devised synthetic approach aims to offer a direct, efficient, and adaptable method for obtaining both pure enantiomers and pure diastereomers. It revolves around utilizing chiral building blocks like
,
-,
,
,
-,
,
-,
,
,
-,
,
-,
,
,
-, and
,
,
-oxazines. By integrating oxazine chemistry with established and innovative transformations, this approach enabled the synthesis of 30 polyhydroxylated amines across various studies conducted between 2007 and 2022.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>38230703</pmid><doi>10.1039/d3ob01624b</doi><tpages>33</tpages><orcidid>https://orcid.org/0000-0003-0085-2994</orcidid><orcidid>https://orcid.org/0000-0001-8611-7776</orcidid><orcidid>https://orcid.org/0000-0003-3982-5264</orcidid></addata></record> |
| fulltext | fulltext |
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| ispartof | Organic & biomolecular chemistry, 2024-01, Vol.22 (5), p.894-926 |
| issn | 1477-0520 1477-0539 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alkaloids Amines Anisomycin Biological activity Diastereoisomers Enantiomers Intermediates Natural products Oxazine Stereoselectivity Synthesis |
| title | Recent advances in the total synthesis of polyhydroxylated alkaloids via chiral oxazines |
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