Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids
Covering: up to the end of 2017 Enantioselective Pd-catalyzed allylic alkylations of prochiral enolates represent a powerful tool for the construction of all-carbon quaternary stereocenters. This review describes the emergence of such reactions as strategic linchpins that enable efficient, stereocon...
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| Veröffentlicht in: | Natural product reports 2018-06, Vol.35 (6), p.559-574 |
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| creator | Pritchett, Beau P Stoltz, Brian M |
| description | Covering: up to the end of 2017
Enantioselective Pd-catalyzed allylic alkylations of prochiral enolates represent a powerful tool for the construction of all-carbon quaternary stereocenters. This review describes the emergence of such reactions as strategic linchpins that enable efficient, stereocontrolled syntheses of
Aspidosperma
and related monoterpene indole alkaloids.
The development of new heterocyclic substrate classes for palladium-catalyzed allylic alkylation has enhanced synthetic access to structurally diverse monoterpene indole alkaloids. |
| doi_str_mv | 10.1039/c7np00069c |
| format | Article |
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Enantioselective Pd-catalyzed allylic alkylations of prochiral enolates represent a powerful tool for the construction of all-carbon quaternary stereocenters. This review describes the emergence of such reactions as strategic linchpins that enable efficient, stereocontrolled syntheses of
Aspidosperma
and related monoterpene indole alkaloids.
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Enantioselective Pd-catalyzed allylic alkylations of prochiral enolates represent a powerful tool for the construction of all-carbon quaternary stereocenters. This review describes the emergence of such reactions as strategic linchpins that enable efficient, stereocontrolled syntheses of
Aspidosperma
and related monoterpene indole alkaloids.
The development of new heterocyclic substrate classes for palladium-catalyzed allylic alkylation has enhanced synthetic access to structurally diverse monoterpene indole alkaloids.</description><subject>Alkaloids</subject><subject>Alkylation</subject><subject>Aspidosperma</subject><subject>Aspidosperma - chemistry</subject><subject>Catalysis</subject><subject>catalytic activity</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Enantiomers</subject><subject>enantioselectivity</subject><subject>Heterocyclic Compounds, 4 or More Rings - chemical synthesis</subject><subject>Heterocyclic Compounds, 4 or More Rings - chemistry</subject><subject>indole alkaloids</subject><subject>Indole Alkaloids - chemical synthesis</subject><subject>Indole Alkaloids - chemistry</subject><subject>Indoles</subject><subject>Molecular Structure</subject><subject>Monoterpenes - chemical synthesis</subject><subject>Monoterpenes - chemistry</subject><subject>monoterpenoids</subject><subject>Palladium</subject><subject>Stereoisomerism</subject><issn>0265-0568</issn><issn>1460-4752</issn><issn>1460-4752</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkk2P1SAUhonRONfRjXsNxo0xqQIttGxMJjfjRzJRF7omFE4dxhYq0EnqL5mfO1zveP1Y6OoQ3oeXw-FF6CElLyip5UvT-pkQIqS5hTa0EaRqWs5uow1hgleEi-4I3UvpghBKWyHuoiMmBe_K0Q26OvXaZxcSjGCyuwQ863HU1i1TZXTW4_odLC5b6-hMqV_XURfc4wja7BYJO4_zOeC0-lKSSzgM-CTNzoY0Q5w01t7ilONi8hJ3TuVsMSm2U_AhQ5zBQ3GxYYTdDXoMzqb76M6gxwQPbuox-vz69NP2bXX24c277clZZTivc6V1P0hhTA3ctIRI2Yqh1wZaS3nXQzv0tJfcGtZJ2YtmaORAu4aYrted0NLUx-jV3nde-gmsAZ9Lk2qObtJxVUE79afi3bn6Ei6VILRuCC8Gz24MYvi2QMpqcslAGaKHsCTFGKOE006w_6OElW9pSEML-vQv9CIs0ZdJFIq3TNRtJwv1fE-ZGFKKMBz6pkTtsqG27fuPP7KxLfDj3196QH-GoQCP9kBM5qD-ClfRn_xLV7Md6mu1-s_h</recordid><startdate>20180620</startdate><enddate>20180620</enddate><creator>Pritchett, Beau P</creator><creator>Stoltz, Brian M</creator><general>Royal Society of Chemistry</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><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>RC3</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-9837-1528</orcidid><orcidid>https://orcid.org/0000-0001-9922-9160</orcidid></search><sort><creationdate>20180620</creationdate><title>Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids</title><author>Pritchett, Beau P ; Stoltz, Brian M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c553t-aabf96cc3e5c7009976fbace7d158be7fb1b95dc2899b64f49f1840c8ba86a9c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alkaloids</topic><topic>Alkylation</topic><topic>Aspidosperma</topic><topic>Aspidosperma - chemistry</topic><topic>Catalysis</topic><topic>catalytic activity</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Enantiomers</topic><topic>enantioselectivity</topic><topic>Heterocyclic Compounds, 4 or More Rings - chemical synthesis</topic><topic>Heterocyclic Compounds, 4 or More Rings - chemistry</topic><topic>indole alkaloids</topic><topic>Indole Alkaloids - chemical synthesis</topic><topic>Indole Alkaloids - chemistry</topic><topic>Indoles</topic><topic>Molecular Structure</topic><topic>Monoterpenes - chemical synthesis</topic><topic>Monoterpenes - chemistry</topic><topic>monoterpenoids</topic><topic>Palladium</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pritchett, Beau P</creatorcontrib><creatorcontrib>Stoltz, Brian M</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><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>Genetics Abstracts</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Natural product reports</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pritchett, Beau P</au><au>Stoltz, Brian M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids</atitle><jtitle>Natural product reports</jtitle><addtitle>Nat Prod Rep</addtitle><date>2018-06-20</date><risdate>2018</risdate><volume>35</volume><issue>6</issue><spage>559</spage><epage>574</epage><pages>559-574</pages><issn>0265-0568</issn><issn>1460-4752</issn><eissn>1460-4752</eissn><abstract>Covering: up to the end of 2017
Enantioselective Pd-catalyzed allylic alkylations of prochiral enolates represent a powerful tool for the construction of all-carbon quaternary stereocenters. This review describes the emergence of such reactions as strategic linchpins that enable efficient, stereocontrolled syntheses of
Aspidosperma
and related monoterpene indole alkaloids.
The development of new heterocyclic substrate classes for palladium-catalyzed allylic alkylation has enhanced synthetic access to structurally diverse monoterpene indole alkaloids.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>29658039</pmid><doi>10.1039/c7np00069c</doi><tpages>16</tpages><orcidid>https://orcid.org/0000-0001-9837-1528</orcidid><orcidid>https://orcid.org/0000-0001-9922-9160</orcidid><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0265-0568 |
| ispartof | Natural product reports, 2018-06, Vol.35 (6), p.559-574 |
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| language | eng |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alkaloids Alkylation Aspidosperma Aspidosperma - chemistry Catalysis catalytic activity Chemical reactions Chemical synthesis Enantiomers enantioselectivity Heterocyclic Compounds, 4 or More Rings - chemical synthesis Heterocyclic Compounds, 4 or More Rings - chemistry indole alkaloids Indole Alkaloids - chemical synthesis Indole Alkaloids - chemistry Indoles Molecular Structure Monoterpenes - chemical synthesis Monoterpenes - chemistry monoterpenoids Palladium Stereoisomerism |
| title | Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids |
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