Total Synthesis of (−)‐Vindorosine
Outlined herein is a novel and scalable synthesis of (−)‐vindorosine based on two key transformations. A highly diastereoselective vinylogous Mannich addition of dioxinone‐derived lithium dienolates with indolyl N‐tert‐butanesulfinyl imines has been developed. In addition, an intramolecular Heathcoc...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2017-09, Vol.56 (40), p.12327-12331 |
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| container_end_page | 12331 |
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| container_issue | 40 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Chen, Wen Yang, Xiao‐Dong Tan, Wen‐Yun Zhang, Xiang‐Yang Liao, Xia‐Li Zhang, Hongbin |
| description | Outlined herein is a novel and scalable synthesis of (−)‐vindorosine based on two key transformations. A highly diastereoselective vinylogous Mannich addition of dioxinone‐derived lithium dienolates with indolyl N‐tert‐butanesulfinyl imines has been developed. In addition, an intramolecular Heathcock/aza‐Prins cyclization was introduced to construct both the C, and the highly substituted E rings for the synthesis of (−)‐vindorosine and related alkaloids.
In total: A new strategy for the synthesis of (−)‐vindorosine and related alkaloids features an asymmetric vinylogous Mannich addition of dioxinone‐derived lithium dienolates to indolyl N‐tert‐butanesulfinyl imines, and an intramolecular Heathcock/aza‐Prins cyclization to construct the C and E rings. Tf=trifluoromethanesulfonyl, THF=tetrahydrofuran. |
| doi_str_mv | 10.1002/anie.201707249 |
| format | Article |
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In total: A new strategy for the synthesis of (−)‐vindorosine and related alkaloids features an asymmetric vinylogous Mannich addition of dioxinone‐derived lithium dienolates to indolyl N‐tert‐butanesulfinyl imines, and an intramolecular Heathcock/aza‐Prins cyclization to construct the C and E rings. Tf=trifluoromethanesulfonyl, THF=tetrahydrofuran.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201707249</identifier><identifier>PMID: 28782228</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Alkaloids ; cyclizations ; heterocycles ; Imines ; Lithium ; natural products ; Synthesis ; total synthesis</subject><ispartof>Angewandte Chemie International Edition, 2017-09, Vol.56 (40), p.12327-12331</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4769-16e84c47f2413290ae108cfd75bdceddf5d154ec19ac779b04ce0fe812f116423</citedby><cites>FETCH-LOGICAL-c4769-16e84c47f2413290ae108cfd75bdceddf5d154ec19ac779b04ce0fe812f116423</cites><orcidid>0000-0002-2516-2634</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.201707249$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201707249$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27928,27929,45578,45579</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28782228$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Wen</creatorcontrib><creatorcontrib>Yang, Xiao‐Dong</creatorcontrib><creatorcontrib>Tan, Wen‐Yun</creatorcontrib><creatorcontrib>Zhang, Xiang‐Yang</creatorcontrib><creatorcontrib>Liao, Xia‐Li</creatorcontrib><creatorcontrib>Zhang, Hongbin</creatorcontrib><title>Total Synthesis of (−)‐Vindorosine</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Outlined herein is a novel and scalable synthesis of (−)‐vindorosine based on two key transformations. A highly diastereoselective vinylogous Mannich addition of dioxinone‐derived lithium dienolates with indolyl N‐tert‐butanesulfinyl imines has been developed. In addition, an intramolecular Heathcock/aza‐Prins cyclization was introduced to construct both the C, and the highly substituted E rings for the synthesis of (−)‐vindorosine and related alkaloids.
In total: A new strategy for the synthesis of (−)‐vindorosine and related alkaloids features an asymmetric vinylogous Mannich addition of dioxinone‐derived lithium dienolates to indolyl N‐tert‐butanesulfinyl imines, and an intramolecular Heathcock/aza‐Prins cyclization to construct the C and E rings. Tf=trifluoromethanesulfonyl, THF=tetrahydrofuran.</description><subject>Alkaloids</subject><subject>cyclizations</subject><subject>heterocycles</subject><subject>Imines</subject><subject>Lithium</subject><subject>natural products</subject><subject>Synthesis</subject><subject>total synthesis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqF0DFLAzEUB_Agiq3V1VEKgtThal4ud0nGUqoWig5W13DNveCV61299CjdHB3Fj9hPYkprBRenvOH3_uT9CTkH2gVK2U1SZNhlFAQVjKsD0oSIQRAKER76mYdhIGQEDXLi3NR7KWl8TBpMCskYk01yNS4XSd5-WhWLV3SZa5e23Vl_fF2v3z9fsiItq9JlBZ6SI5vkDs92b4s83w7G_ftg9Hg37PdGgeEiVgHEKLkfLeMQMkUTBCqNTUU0SQ2mqY1SiDgaUIkRQk0oN0gtSmAWIOYsbJHONndelW81uoWeZc5gnicFlrXToFispL-ce3r5h07Luir877zilHPGufCqu1XGH-IqtHpeZbOkWmmgetOg3jSo9w36hYtdbD2ZYbrnP5V5oLZgmeW4-idO9x6Gg9_wb9bkfEQ</recordid><startdate>20170925</startdate><enddate>20170925</enddate><creator>Chen, Wen</creator><creator>Yang, Xiao‐Dong</creator><creator>Tan, Wen‐Yun</creator><creator>Zhang, Xiang‐Yang</creator><creator>Liao, Xia‐Li</creator><creator>Zhang, Hongbin</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/0000-0002-2516-2634</orcidid></search><sort><creationdate>20170925</creationdate><title>Total Synthesis of (−)‐Vindorosine</title><author>Chen, Wen ; Yang, Xiao‐Dong ; Tan, Wen‐Yun ; Zhang, Xiang‐Yang ; Liao, Xia‐Li ; Zhang, Hongbin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4769-16e84c47f2413290ae108cfd75bdceddf5d154ec19ac779b04ce0fe812f116423</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alkaloids</topic><topic>cyclizations</topic><topic>heterocycles</topic><topic>Imines</topic><topic>Lithium</topic><topic>natural products</topic><topic>Synthesis</topic><topic>total synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Wen</creatorcontrib><creatorcontrib>Yang, Xiao‐Dong</creatorcontrib><creatorcontrib>Tan, Wen‐Yun</creatorcontrib><creatorcontrib>Zhang, Xiang‐Yang</creatorcontrib><creatorcontrib>Liao, Xia‐Li</creatorcontrib><creatorcontrib>Zhang, Hongbin</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>Chen, Wen</au><au>Yang, Xiao‐Dong</au><au>Tan, Wen‐Yun</au><au>Zhang, Xiang‐Yang</au><au>Liao, Xia‐Li</au><au>Zhang, Hongbin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of (−)‐Vindorosine</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2017-09-25</date><risdate>2017</risdate><volume>56</volume><issue>40</issue><spage>12327</spage><epage>12331</epage><pages>12327-12331</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Outlined herein is a novel and scalable synthesis of (−)‐vindorosine based on two key transformations. A highly diastereoselective vinylogous Mannich addition of dioxinone‐derived lithium dienolates with indolyl N‐tert‐butanesulfinyl imines has been developed. In addition, an intramolecular Heathcock/aza‐Prins cyclization was introduced to construct both the C, and the highly substituted E rings for the synthesis of (−)‐vindorosine and related alkaloids.
In total: A new strategy for the synthesis of (−)‐vindorosine and related alkaloids features an asymmetric vinylogous Mannich addition of dioxinone‐derived lithium dienolates to indolyl N‐tert‐butanesulfinyl imines, and an intramolecular Heathcock/aza‐Prins cyclization to construct the C and E rings. Tf=trifluoromethanesulfonyl, THF=tetrahydrofuran.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>28782228</pmid><doi>10.1002/anie.201707249</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-2516-2634</orcidid></addata></record> |
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| language | eng |
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| source | Wiley Online Library All Journals |
| subjects | Alkaloids cyclizations heterocycles Imines Lithium natural products Synthesis total synthesis |
| title | Total Synthesis of (−)‐Vindorosine |
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