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Cross dehydrogenative coupling of sugar enol ethers with terminal alkenes in the synthesis of pseudo-disaccharides, chiral oxadecalins and a conjugated triene
An efficient strategy for the synthesis of C-2 and C-3 branched sugar dienes via cross dehydrogenative coupling of sugar enol ethers with terminal alkenes was developed. Both pyran and furan based enol ethers coupled smoothly with electron rich as well as deficient alkene sources yielding sugar dien...
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| Published in: | Organic & biomolecular chemistry 2018-04, Vol.16 (15), p.2666-2677 |
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| Main Authors: | , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c337t-a94c7bbe7d90f9ccc61749d5be147a10e5137fe1a7643424ba0c4db3691d688e3 |
| container_end_page | 2677 |
| container_issue | 15 |
| container_start_page | 2666 |
| container_title | Organic & biomolecular chemistry |
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| creator | Hussain, Nazar Babu Tatina, Madhu Mukherjee, Debaraj |
| description | An efficient strategy for the synthesis of C-2 and C-3 branched sugar dienes
via
cross dehydrogenative coupling of sugar enol ethers with terminal alkenes was developed. Both pyran and furan based enol ethers coupled smoothly with electron rich as well as deficient alkene sources yielding sugar dienes with complete
E
-stereoselectivity. This coupling reaction was applied successfully for the synthesis of orthogonally protected pseudo-C-saccharides as an alternative to olefin metathesis. Substrate scope was further enhanced by reacting exoglycals with methyl acrylate to generate C-5 branched sugars with moderate diastereoselectivity. These diene subunits were reacted with maleic anhydride under [4 + 2] cycloaddition conditions to generate highly functionalised chiral oxadecalin cores. Finally, utilizing this C-C bond formation, a sugar based conjugated triene was synthesized in excellent yield and selectivity.
An efficient strategy for the synthesis of C-2 and C-3 branched sugar dienes
via
cross dehydrogenative coupling of sugar enol ethers with terminal alkenes was developed. |
| doi_str_mv | 10.1039/c8ob00168e |
| format | article |
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via
cross dehydrogenative coupling of sugar enol ethers with terminal alkenes was developed. Both pyran and furan based enol ethers coupled smoothly with electron rich as well as deficient alkene sources yielding sugar dienes with complete
E
-stereoselectivity. This coupling reaction was applied successfully for the synthesis of orthogonally protected pseudo-C-saccharides as an alternative to olefin metathesis. Substrate scope was further enhanced by reacting exoglycals with methyl acrylate to generate C-5 branched sugars with moderate diastereoselectivity. These diene subunits were reacted with maleic anhydride under [4 + 2] cycloaddition conditions to generate highly functionalised chiral oxadecalin cores. Finally, utilizing this C-C bond formation, a sugar based conjugated triene was synthesized in excellent yield and selectivity.
An efficient strategy for the synthesis of C-2 and C-3 branched sugar dienes
via
cross dehydrogenative coupling of sugar enol ethers with terminal alkenes was developed.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c8ob00168e</identifier><identifier>PMID: 29577133</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkenes ; Anhydrides ; Carbohydrates ; Chemical industry ; Chemical synthesis ; Coupling ; Cycloaddition ; Dehydrogenation ; Dienes ; Disaccharides ; Ethers ; Maleic anhydride ; Metathesis ; Saccharides ; Stereoselectivity ; Substrates ; Sugar</subject><ispartof>Organic & biomolecular chemistry, 2018-04, Vol.16 (15), p.2666-2677</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-a94c7bbe7d90f9ccc61749d5be147a10e5137fe1a7643424ba0c4db3691d688e3</citedby><cites>FETCH-LOGICAL-c337t-a94c7bbe7d90f9ccc61749d5be147a10e5137fe1a7643424ba0c4db3691d688e3</cites><orcidid>0000-0002-2162-7465</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29577133$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hussain, Nazar</creatorcontrib><creatorcontrib>Babu Tatina, Madhu</creatorcontrib><creatorcontrib>Mukherjee, Debaraj</creatorcontrib><title>Cross dehydrogenative coupling of sugar enol ethers with terminal alkenes in the synthesis of pseudo-disaccharides, chiral oxadecalins and a conjugated triene</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>An efficient strategy for the synthesis of C-2 and C-3 branched sugar dienes
via
cross dehydrogenative coupling of sugar enol ethers with terminal alkenes was developed. Both pyran and furan based enol ethers coupled smoothly with electron rich as well as deficient alkene sources yielding sugar dienes with complete
E
-stereoselectivity. This coupling reaction was applied successfully for the synthesis of orthogonally protected pseudo-C-saccharides as an alternative to olefin metathesis. Substrate scope was further enhanced by reacting exoglycals with methyl acrylate to generate C-5 branched sugars with moderate diastereoselectivity. These diene subunits were reacted with maleic anhydride under [4 + 2] cycloaddition conditions to generate highly functionalised chiral oxadecalin cores. Finally, utilizing this C-C bond formation, a sugar based conjugated triene was synthesized in excellent yield and selectivity.
An efficient strategy for the synthesis of C-2 and C-3 branched sugar dienes
via
cross dehydrogenative coupling of sugar enol ethers with terminal alkenes was developed.</description><subject>Alkenes</subject><subject>Anhydrides</subject><subject>Carbohydrates</subject><subject>Chemical industry</subject><subject>Chemical synthesis</subject><subject>Coupling</subject><subject>Cycloaddition</subject><subject>Dehydrogenation</subject><subject>Dienes</subject><subject>Disaccharides</subject><subject>Ethers</subject><subject>Maleic anhydride</subject><subject>Metathesis</subject><subject>Saccharides</subject><subject>Stereoselectivity</subject><subject>Substrates</subject><subject>Sugar</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpdkU9v1DAQxS0EoqVw4Q6yxKVCBOw4G8fHsip_pEq9wDma2JONl6y9eJLCfhk-Kw5bFonTWJrfvCe_x9hzKd5Kocw728ROCFk3-ICdy0rrQqyUeXh6l-KMPSHaZsbounrMzkqz0loqdc5-rVMk4g6Hg0txgwEmf4fcxnk_-rDhsec0byBxDHHkOA2YiP_w08AnTDsfYOQwfsOAxH3gec3pEPIgT8vtnnB2sXCewNoBkndIb7gdfMqH8Sc4tJB9iENwHLJt2Ga3CR2fks-qT9mjHkbCZ_fzgn39cP1l_am4uf34eX11U1il9FSAqazuOtTOiN5Ya2upK-NWHeYIQApcSaV7lJC_r6qy6kDYynWqNtLVTYPqgl0edfcpfp-RpnbnyeI4QsA4U1sK2dS1EUJk9NV_6DbOKQexUKWWVd3IhXp9pOySb8K-3Se_g3RopWiX1tp1c_v-T2vXGX55Lzl3O3Qn9G9NGXhxBBLZ0_Zf7eo3S-2fJQ</recordid><startdate>20180418</startdate><enddate>20180418</enddate><creator>Hussain, Nazar</creator><creator>Babu Tatina, Madhu</creator><creator>Mukherjee, Debaraj</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/0000-0002-2162-7465</orcidid></search><sort><creationdate>20180418</creationdate><title>Cross dehydrogenative coupling of sugar enol ethers with terminal alkenes in the synthesis of pseudo-disaccharides, chiral oxadecalins and a conjugated triene</title><author>Hussain, Nazar ; Babu Tatina, Madhu ; Mukherjee, Debaraj</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-a94c7bbe7d90f9ccc61749d5be147a10e5137fe1a7643424ba0c4db3691d688e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alkenes</topic><topic>Anhydrides</topic><topic>Carbohydrates</topic><topic>Chemical industry</topic><topic>Chemical synthesis</topic><topic>Coupling</topic><topic>Cycloaddition</topic><topic>Dehydrogenation</topic><topic>Dienes</topic><topic>Disaccharides</topic><topic>Ethers</topic><topic>Maleic anhydride</topic><topic>Metathesis</topic><topic>Saccharides</topic><topic>Stereoselectivity</topic><topic>Substrates</topic><topic>Sugar</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hussain, Nazar</creatorcontrib><creatorcontrib>Babu Tatina, Madhu</creatorcontrib><creatorcontrib>Mukherjee, Debaraj</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>Hussain, Nazar</au><au>Babu Tatina, Madhu</au><au>Mukherjee, Debaraj</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cross dehydrogenative coupling of sugar enol ethers with terminal alkenes in the synthesis of pseudo-disaccharides, chiral oxadecalins and a conjugated triene</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2018-04-18</date><risdate>2018</risdate><volume>16</volume><issue>15</issue><spage>2666</spage><epage>2677</epage><pages>2666-2677</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>An efficient strategy for the synthesis of C-2 and C-3 branched sugar dienes
via
cross dehydrogenative coupling of sugar enol ethers with terminal alkenes was developed. Both pyran and furan based enol ethers coupled smoothly with electron rich as well as deficient alkene sources yielding sugar dienes with complete
E
-stereoselectivity. This coupling reaction was applied successfully for the synthesis of orthogonally protected pseudo-C-saccharides as an alternative to olefin metathesis. Substrate scope was further enhanced by reacting exoglycals with methyl acrylate to generate C-5 branched sugars with moderate diastereoselectivity. These diene subunits were reacted with maleic anhydride under [4 + 2] cycloaddition conditions to generate highly functionalised chiral oxadecalin cores. Finally, utilizing this C-C bond formation, a sugar based conjugated triene was synthesized in excellent yield and selectivity.
An efficient strategy for the synthesis of C-2 and C-3 branched sugar dienes
via
cross dehydrogenative coupling of sugar enol ethers with terminal alkenes was developed.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>29577133</pmid><doi>10.1039/c8ob00168e</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0002-2162-7465</orcidid></addata></record> |
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| ispartof | Organic & biomolecular chemistry, 2018-04, Vol.16 (15), p.2666-2677 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_pubmed_primary_29577133 |
| source | Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list) |
| subjects | Alkenes Anhydrides Carbohydrates Chemical industry Chemical synthesis Coupling Cycloaddition Dehydrogenation Dienes Disaccharides Ethers Maleic anhydride Metathesis Saccharides Stereoselectivity Substrates Sugar |
| title | Cross dehydrogenative coupling of sugar enol ethers with terminal alkenes in the synthesis of pseudo-disaccharides, chiral oxadecalins and a conjugated triene |
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