Stereochemical Complexity in Oxocarbenium-Ion-Initiated Cascade Annulations for the Synthesis of the ABCD Core of Mattogrossine

Mattogrossine is an indole alkaloid isolated from Strychnos mattogrossensis that contains an unusual tetrahydrofuran ring with a concomitant hemiacetal in its structure. While tetrahydrofuran intermediates have been used in the synthesis of other strychnos alkaloids, no investigations have been perf...

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Veröffentlicht in:	Journal of organic chemistry 2017-04, Vol.82 (8), p.4477-4483
Hauptverfasser:	Kong, Aidi, Andreansky, Eric S, Blakey, Simon B
Format:	Artikel
Sprache:	eng
Schlagworte:	Cyclization Indole Alkaloids - chemical synthesis Indole Alkaloids - chemistry Methane - analogs & derivatives Methane - chemistry Stereoisomerism
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container_title	Journal of organic chemistry
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creator	Kong, Aidi Andreansky, Eric S Blakey, Simon B
description	Mattogrossine is an indole alkaloid isolated from Strychnos mattogrossensis that contains an unusual tetrahydrofuran ring with a concomitant hemiacetal in its structure. While tetrahydrofuran intermediates have been used in the synthesis of other strychnos alkaloids, no investigations have been performed into the synthesis of alkaloids containing this structure. We have developed an oxocarbenium-ion-initiated cascade annulation that provides us access to the ABCD ring structure of mattogrossine.
doi_str_mv	10.1021/acs.joc.7b00503
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Org. Chem</addtitle><description>Mattogrossine is an indole alkaloid isolated from Strychnos mattogrossensis that contains an unusual tetrahydrofuran ring with a concomitant hemiacetal in its structure. While tetrahydrofuran intermediates have been used in the synthesis of other strychnos alkaloids, no investigations have been performed into the synthesis of alkaloids containing this structure. We have developed an oxocarbenium-ion-initiated cascade annulation that provides us access to the ABCD ring structure of mattogrossine.</description><subject>Cyclization</subject><subject>Indole Alkaloids - chemical synthesis</subject><subject>Indole Alkaloids - chemistry</subject><subject>Methane - analogs & derivatives</subject><subject>Methane - chemistry</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kD1v2zAQhomiQeMknbsFHAsEsknRlKjRVb4MJPDgdBZI6pTQkEiXpIB46l8vXTndessBh-de3D0IfaNkTklOF1KH-c7peakI4YR9QjPKc5IVFVl-RjNC8jxjecHO0UUIO5KKc_4FneeCVSyBM_R7G8GD028wGC17XLth38O7iQdsLN68Oy29AmvGIVs7m62tiUZGaHEtg5Yt4JW1Yy-jcTbgznkc3wBvDza1YAJ23d_B6kd9m6I9HAfPMkb36l0IxsIVOutkH-DrqV-in_d3L_Vj9rR5WNerp0wyxmJWlflSKSVBtZLSlnLoFFFt2QkuKkG0yLtWa02qsiqkoFQLKEHrsmoLUqqOsUv0fcrde_drhBCbwQQNfS8tuDE0VIiC8YLTZUIXE6qPN3romr03g_SHhpLmaL1J1ptkvTlZTxvXp_BRDdD-4z80J-BmAqbN0dv063_j_gAad4-6</recordid><startdate>20170421</startdate><enddate>20170421</enddate><creator>Kong, Aidi</creator><creator>Andreansky, Eric S</creator><creator>Blakey, Simon B</creator><general>American Chemical Society</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>7X8</scope><orcidid>https://orcid.org/0000-0002-4100-8610</orcidid></search><sort><creationdate>20170421</creationdate><title>Stereochemical Complexity in Oxocarbenium-Ion-Initiated Cascade Annulations for the Synthesis of the ABCD Core of Mattogrossine</title><author>Kong, Aidi ; Andreansky, Eric S ; Blakey, Simon B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-9724bbbaebda11d15efb0bd7f858980c82fdccc09796a811c8e7ecc79d607bf33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Cyclization</topic><topic>Indole Alkaloids - chemical synthesis</topic><topic>Indole Alkaloids - chemistry</topic><topic>Methane - analogs & derivatives</topic><topic>Methane - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kong, Aidi</creatorcontrib><creatorcontrib>Andreansky, Eric S</creatorcontrib><creatorcontrib>Blakey, Simon B</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kong, Aidi</au><au>Andreansky, Eric S</au><au>Blakey, Simon B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereochemical Complexity in Oxocarbenium-Ion-Initiated Cascade Annulations for the Synthesis of the ABCD Core of Mattogrossine</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. 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subjects	Cyclization Indole Alkaloids - chemical synthesis Indole Alkaloids - chemistry Methane - analogs & derivatives Methane - chemistry Stereoisomerism
title	Stereochemical Complexity in Oxocarbenium-Ion-Initiated Cascade Annulations for the Synthesis of the ABCD Core of Mattogrossine
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