Total Synthesis of Cryptotrione
The total synthesis of cryptotrione (1) was enabled by substrate‐controlled diastereoselective construction of the bicyclo[3.1.0]hexene framework through platinum‐catalyzed enyne cycloisomerization and Lewis acid induced polyene cyclization to construct the abietane‐type tricyclic diterpene skeleton...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2020-11, Vol.59 (45), p.19929-19933 |
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| container_end_page | 19933 |
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| container_issue | 45 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Lyu, Mao‐Yun Zhong, Zhuliang Lo, Vanessa Kar‐Yan Wong, Henry N. C. Peng, Xiao‐Shui |
| description | The total synthesis of cryptotrione (1) was enabled by substrate‐controlled diastereoselective construction of the bicyclo[3.1.0]hexene framework through platinum‐catalyzed enyne cycloisomerization and Lewis acid induced polyene cyclization to construct the abietane‐type tricyclic diterpene skeleton. The stereogenic tertiary carbon center in the side chain was installed in a diastereodivergent manner by conjugate addition reactions.
A platinum‐catalyzed enyne cycloisomerization reaction to construct the bicyclo[3.1.0]hexane system enabled the total synthesis of cryptotrione from commercially available homoveratric acid in a diastereoselective and diastereodivergent manner (see scheme). This strategy would be practical for synthesizing other members of the structurally unprecedented cryptotrione family. |
| doi_str_mv | 10.1002/anie.202009255 |
| format | Article |
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A platinum‐catalyzed enyne cycloisomerization reaction to construct the bicyclo[3.1.0]hexane system enabled the total synthesis of cryptotrione from commercially available homoveratric acid in a diastereoselective and diastereodivergent manner (see scheme). This strategy would be practical for synthesizing other members of the structurally unprecedented cryptotrione family.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202009255</identifier><identifier>PMID: 32692466</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>cyclization ; Diterpenes ; enynes ; Isomerization ; Lewis acid ; Platinum ; Stereoselectivity ; Substrates ; Synthesis ; terpenoids ; total synthesis</subject><ispartof>Angewandte Chemie International Edition, 2020-11, Vol.59 (45), p.19929-19933</ispartof><rights>2020 Wiley‐VCH GmbH</rights><rights>2020 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4105-f2a3c0a1616edfca2b634984995426ae6b6a53e880b6ba3dcc13d29f35becc5b3</citedby><cites>FETCH-LOGICAL-c4105-f2a3c0a1616edfca2b634984995426ae6b6a53e880b6ba3dcc13d29f35becc5b3</cites><orcidid>0000-0002-3763-3085</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.202009255$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202009255$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32692466$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lyu, Mao‐Yun</creatorcontrib><creatorcontrib>Zhong, Zhuliang</creatorcontrib><creatorcontrib>Lo, Vanessa Kar‐Yan</creatorcontrib><creatorcontrib>Wong, Henry N. C.</creatorcontrib><creatorcontrib>Peng, Xiao‐Shui</creatorcontrib><title>Total Synthesis of Cryptotrione</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>The total synthesis of cryptotrione (1) was enabled by substrate‐controlled diastereoselective construction of the bicyclo[3.1.0]hexene framework through platinum‐catalyzed enyne cycloisomerization and Lewis acid induced polyene cyclization to construct the abietane‐type tricyclic diterpene skeleton. The stereogenic tertiary carbon center in the side chain was installed in a diastereodivergent manner by conjugate addition reactions.
A platinum‐catalyzed enyne cycloisomerization reaction to construct the bicyclo[3.1.0]hexane system enabled the total synthesis of cryptotrione from commercially available homoveratric acid in a diastereoselective and diastereodivergent manner (see scheme). This strategy would be practical for synthesizing other members of the structurally unprecedented cryptotrione family.</description><subject>cyclization</subject><subject>Diterpenes</subject><subject>enynes</subject><subject>Isomerization</subject><subject>Lewis acid</subject><subject>Platinum</subject><subject>Stereoselectivity</subject><subject>Substrates</subject><subject>Synthesis</subject><subject>terpenoids</subject><subject>total synthesis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkE1Lw0AQhhdRbK1ePWrBi5fU_W72WELVQtGD9bxsNhNMSbN1N0Hy793SWsGLMDBzeOad4UHomuAJwZg-mKaCCcUUY0WFOEFDIihJ2HTKTuPMGUumqSADdBHCOvJpiuU5GjAqFeVSDtHtyrWmHr_1TfsBoQpjV44z329b1_rKNXCJzkpTB7g69BF6f5yvsudk-fq0yGbLxHKCRVJSwyw2RBIJRWkNzSXjKuVKCU6lAZlLIxjE87nMDSusJaygqmQiB2tFzkbofp-79e6zg9DqTRUs1LVpwHVBU05FqkQqWUTv_qBr1_kmfhcpwbHiLNYITfaU9S4ED6Xe-mpjfK8J1jt1eqdOH9XFhZtDbJdvoDjiP64ioPbAV1VD_0-cnr0s5r_h33RneL8</recordid><startdate>20201102</startdate><enddate>20201102</enddate><creator>Lyu, Mao‐Yun</creator><creator>Zhong, Zhuliang</creator><creator>Lo, Vanessa Kar‐Yan</creator><creator>Wong, Henry N. C.</creator><creator>Peng, Xiao‐Shui</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3763-3085</orcidid></search><sort><creationdate>20201102</creationdate><title>Total Synthesis of Cryptotrione</title><author>Lyu, Mao‐Yun ; Zhong, Zhuliang ; Lo, Vanessa Kar‐Yan ; Wong, Henry N. C. ; Peng, Xiao‐Shui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4105-f2a3c0a1616edfca2b634984995426ae6b6a53e880b6ba3dcc13d29f35becc5b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>cyclization</topic><topic>Diterpenes</topic><topic>enynes</topic><topic>Isomerization</topic><topic>Lewis acid</topic><topic>Platinum</topic><topic>Stereoselectivity</topic><topic>Substrates</topic><topic>Synthesis</topic><topic>terpenoids</topic><topic>total synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lyu, Mao‐Yun</creatorcontrib><creatorcontrib>Zhong, Zhuliang</creatorcontrib><creatorcontrib>Lo, Vanessa Kar‐Yan</creatorcontrib><creatorcontrib>Wong, Henry N. C.</creatorcontrib><creatorcontrib>Peng, Xiao‐Shui</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lyu, Mao‐Yun</au><au>Zhong, Zhuliang</au><au>Lo, Vanessa Kar‐Yan</au><au>Wong, Henry N. C.</au><au>Peng, Xiao‐Shui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of Cryptotrione</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2020-11-02</date><risdate>2020</risdate><volume>59</volume><issue>45</issue><spage>19929</spage><epage>19933</epage><pages>19929-19933</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The total synthesis of cryptotrione (1) was enabled by substrate‐controlled diastereoselective construction of the bicyclo[3.1.0]hexene framework through platinum‐catalyzed enyne cycloisomerization and Lewis acid induced polyene cyclization to construct the abietane‐type tricyclic diterpene skeleton. The stereogenic tertiary carbon center in the side chain was installed in a diastereodivergent manner by conjugate addition reactions.
A platinum‐catalyzed enyne cycloisomerization reaction to construct the bicyclo[3.1.0]hexane system enabled the total synthesis of cryptotrione from commercially available homoveratric acid in a diastereoselective and diastereodivergent manner (see scheme). This strategy would be practical for synthesizing other members of the structurally unprecedented cryptotrione family.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>32692466</pmid><doi>10.1002/anie.202009255</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-3763-3085</orcidid></addata></record> |
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| subjects | cyclization Diterpenes enynes Isomerization Lewis acid Platinum Stereoselectivity Substrates Synthesis terpenoids total synthesis |
| title | Total Synthesis of Cryptotrione |
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