Asymmetric construction of six vicinal stereogenic centers on hexahydroxanthones via organocatalytic one-pot reactions
Inspired by the chemistry and biology of hexahydroxanthones, herein we report an organocatalytic Michael–Michael–Aldol-decarboxylation reaction that provides efficient access to biologically interesting fully substituted hexahydroxanthones bearing six contiguous stereogenic centers from readily acce...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2021-07, Vol.57 (55), p.6764-6767 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Zhang, Min He, Xue-Wen Xiong, Ya Zuo, Xiong Zhou, Wei Liu, Xiong-Li |
| description | Inspired by the chemistry and biology of hexahydroxanthones, herein we report an organocatalytic Michael–Michael–Aldol-decarboxylation reaction that provides efficient access to biologically interesting fully substituted hexahydroxanthones bearing six contiguous stereogenic centers from readily accessible materials in acceptable yields (up to 63%) and excellent stereoselectivities (up to 10 : 1 dr and >99% ee). In other words, the reaction efficiently produces three chemical bonds and up to six vicinal stereogenic centers in a one-pot operation. In particular, to our knowledge, this is an asymmetric organocatalytic strategy enabling the first construction of six vicinal stereogenic centers on non-spirocyclic hexahydroxanthone frameworks. |
| doi_str_mv | 10.1039/d1cc02570h |
| format | Article |
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In other words, the reaction efficiently produces three chemical bonds and up to six vicinal stereogenic centers in a one-pot operation. 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In other words, the reaction efficiently produces three chemical bonds and up to six vicinal stereogenic centers in a one-pot operation. In particular, to our knowledge, this is an asymmetric organocatalytic strategy enabling the first construction of six vicinal stereogenic centers on non-spirocyclic hexahydroxanthone frameworks.</description><subject>Aldehydes</subject><subject>Asymmetry</subject><subject>Chemical bonds</subject><subject>Crystallography</subject><subject>Decarboxylation</subject><subject>Single crystals</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdkU1LxDAQhosouK5e_AUBLyJU89UmPS71Y4UFLwreSpom2y5tsibpsv33Znc9OZeZYZ73hZdJklsEHxEkxVODpIQ4Y7A9S2aI5DTNKP8-P8xZkTJCs8vkyvsNjIUyPkt2Cz8Ngwquk0Ba44MbZeisAVYD3-3BrpOdET3wQTll18ocOGXi5kGkWrUX7dQ4uxcmtNYoHxUCWLcWxkoRRD-FqIiHdGsDcEoc3f11cqFF79XNX58nX68vn-UyXX28vZeLVSoxxiFlUiDRZLiplcA0a3AMV2CiqeI5ZrChOM8bSjWnBa9ZXTOiGdIFgrkokK45mSf3J9-tsz-j8qEaOi9V3wuj7OgrnFHEeI44iujdP3RjRxezH6kCYQI5jtTDiZLOeu-UrrauG4SbKgSrwwuqZ1SWxxcsyS_mZ3uq</recordid><startdate>20210708</startdate><enddate>20210708</enddate><creator>Zhang, Min</creator><creator>He, Xue-Wen</creator><creator>Xiong, Ya</creator><creator>Zuo, Xiong</creator><creator>Zhou, Wei</creator><creator>Liu, Xiong-Li</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-5188-6970</orcidid></search><sort><creationdate>20210708</creationdate><title>Asymmetric construction of six vicinal stereogenic centers on hexahydroxanthones via organocatalytic one-pot reactions</title><author>Zhang, Min ; He, Xue-Wen ; Xiong, Ya ; Zuo, Xiong ; Zhou, Wei ; Liu, Xiong-Li</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c222t-7ca1ad52dbea245d2c02923f4e86270d4266d44f8498b7bb73f71f9106a91fb83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aldehydes</topic><topic>Asymmetry</topic><topic>Chemical bonds</topic><topic>Crystallography</topic><topic>Decarboxylation</topic><topic>Single crystals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Min</creatorcontrib><creatorcontrib>He, Xue-Wen</creatorcontrib><creatorcontrib>Xiong, Ya</creatorcontrib><creatorcontrib>Zuo, Xiong</creatorcontrib><creatorcontrib>Zhou, Wei</creatorcontrib><creatorcontrib>Liu, Xiong-Li</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Min</au><au>He, Xue-Wen</au><au>Xiong, Ya</au><au>Zuo, Xiong</au><au>Zhou, Wei</au><au>Liu, Xiong-Li</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric construction of six vicinal stereogenic centers on hexahydroxanthones via organocatalytic one-pot reactions</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><date>2021-07-08</date><risdate>2021</risdate><volume>57</volume><issue>55</issue><spage>6764</spage><epage>6767</epage><pages>6764-6767</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>Inspired by the chemistry and biology of hexahydroxanthones, herein we report an organocatalytic Michael–Michael–Aldol-decarboxylation reaction that provides efficient access to biologically interesting fully substituted hexahydroxanthones bearing six contiguous stereogenic centers from readily accessible materials in acceptable yields (up to 63%) and excellent stereoselectivities (up to 10 : 1 dr and >99% ee). In other words, the reaction efficiently produces three chemical bonds and up to six vicinal stereogenic centers in a one-pot operation. In particular, to our knowledge, this is an asymmetric organocatalytic strategy enabling the first construction of six vicinal stereogenic centers on non-spirocyclic hexahydroxanthone frameworks.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1cc02570h</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0001-5188-6970</orcidid></addata></record> |
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| ispartof | Chemical communications (Cambridge, England), 2021-07, Vol.57 (55), p.6764-6767 |
| issn | 1359-7345 1364-548X |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aldehydes Asymmetry Chemical bonds Crystallography Decarboxylation Single crystals |
| title | Asymmetric construction of six vicinal stereogenic centers on hexahydroxanthones via organocatalytic one-pot reactions |
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