Organocatalytic Enantioselective Pictet–Spengler Approach to Biologically Relevant 1‑Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids
A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet–Spengler reactions (86–92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfeny...
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| Veröffentlicht in: | Journal of organic chemistry 2015-05, Vol.80 (10), p.5125-5132 |
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| container_title | Journal of organic chemistry |
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| creator | Ruiz-Olalla, Andrea Würdemann, Martien A Wanner, Martin J Ingemann, Steen van Maarseveen, Jan H Hiemstra, Henk |
| description | A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet–Spengler reactions (86–92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine. |
| doi_str_mv | 10.1021/acs.joc.5b00509 |
| format | Article |
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The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.5b00509</identifier><identifier>PMID: 25909585</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkaloids - chemical synthesis ; Alkaloids - chemistry ; Benzylisoquinolines - chemistry ; Biological Products - chemical synthesis ; Biological Products - chemistry ; Catalysis ; Cyclization ; Ethylamines - chemistry ; Isoquinolines - chemistry ; Molecular Structure ; Organic Chemistry Phenomena ; Stereoisomerism ; Tetrahydroisoquinolines - chemical synthesis ; Tetrahydroisoquinolines - chemistry</subject><ispartof>Journal of organic chemistry, 2015-05, Vol.80 (10), p.5125-5132</ispartof><rights>Copyright © American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a440t-20c544dd7532326d1b1856491444b0ce3f8704eb7d84b14cbcabf7c92317f99b3</citedby><cites>FETCH-LOGICAL-a440t-20c544dd7532326d1b1856491444b0ce3f8704eb7d84b14cbcabf7c92317f99b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.5b00509$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.5b00509$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25909585$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ruiz-Olalla, Andrea</creatorcontrib><creatorcontrib>Würdemann, Martien A</creatorcontrib><creatorcontrib>Wanner, Martin J</creatorcontrib><creatorcontrib>Ingemann, Steen</creatorcontrib><creatorcontrib>van Maarseveen, Jan H</creatorcontrib><creatorcontrib>Hiemstra, Henk</creatorcontrib><title>Organocatalytic Enantioselective Pictet–Spengler Approach to Biologically Relevant 1‑Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet–Spengler reactions (86–92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.</description><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - chemistry</subject><subject>Benzylisoquinolines - chemistry</subject><subject>Biological Products - chemical synthesis</subject><subject>Biological Products - chemistry</subject><subject>Catalysis</subject><subject>Cyclization</subject><subject>Ethylamines - chemistry</subject><subject>Isoquinolines - chemistry</subject><subject>Molecular Structure</subject><subject>Organic Chemistry Phenomena</subject><subject>Stereoisomerism</subject><subject>Tetrahydroisoquinolines - chemical synthesis</subject><subject>Tetrahydroisoquinolines - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kL9PGzEYhi1UBAE6d6turEQu2D77fowB0VIJiarQ-WT7vgsGxw62D-k6ZWSt-A_zl9QoKVs9fF6e95XeB6FPBM8IpuRMqDB7cGrGJcYcN3toQjjFedlg9gFNMKY0L2hZHKKjEB5wepzzA3RIeYMbXvMJernxC2GdElGYMWqVXVpho3YBDKionyH7oVWEuFm_3q7ALgz4bL5aeSfUfRZddq6dcQuthDFj9jOFnlM8I5v1n3Owv0eTkymdFlOW30H04n7svNPBPQ3aOqMtZHPzKIzTXThB-70wAT7u_mP06-vl3cVVfn3z7fvF_DoXjOGYU6w4Y11X8YKmZR2RpOYlawhjTGIFRV9XmIGsuppJwpRUQvaVamhBqr5pZHGMvmx704anAUJslzooMEZYcENoSVkTWqZTJfRsiyrvQvDQtyuvl8KPLcHtm_426W-T_nanPyU-78oHuYTunf_nOwGnW2CbHLxNW_9b9xftppQH</recordid><startdate>20150515</startdate><enddate>20150515</enddate><creator>Ruiz-Olalla, Andrea</creator><creator>Würdemann, Martien A</creator><creator>Wanner, Martin J</creator><creator>Ingemann, Steen</creator><creator>van Maarseveen, Jan H</creator><creator>Hiemstra, Henk</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></search><sort><creationdate>20150515</creationdate><title>Organocatalytic Enantioselective Pictet–Spengler Approach to Biologically Relevant 1‑Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids</title><author>Ruiz-Olalla, Andrea ; Würdemann, Martien A ; Wanner, Martin J ; Ingemann, Steen ; van Maarseveen, Jan H ; Hiemstra, Henk</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a440t-20c544dd7532326d1b1856491444b0ce3f8704eb7d84b14cbcabf7c92317f99b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Alkaloids - chemical synthesis</topic><topic>Alkaloids - chemistry</topic><topic>Benzylisoquinolines - chemistry</topic><topic>Biological Products - chemical synthesis</topic><topic>Biological Products - chemistry</topic><topic>Catalysis</topic><topic>Cyclization</topic><topic>Ethylamines - chemistry</topic><topic>Isoquinolines - chemistry</topic><topic>Molecular Structure</topic><topic>Organic Chemistry Phenomena</topic><topic>Stereoisomerism</topic><topic>Tetrahydroisoquinolines - chemical synthesis</topic><topic>Tetrahydroisoquinolines - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ruiz-Olalla, Andrea</creatorcontrib><creatorcontrib>Würdemann, Martien A</creatorcontrib><creatorcontrib>Wanner, Martin J</creatorcontrib><creatorcontrib>Ingemann, Steen</creatorcontrib><creatorcontrib>van Maarseveen, Jan H</creatorcontrib><creatorcontrib>Hiemstra, Henk</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>Ruiz-Olalla, Andrea</au><au>Würdemann, Martien A</au><au>Wanner, Martin J</au><au>Ingemann, Steen</au><au>van Maarseveen, Jan H</au><au>Hiemstra, Henk</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Organocatalytic Enantioselective Pictet–Spengler Approach to Biologically Relevant 1‑Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2015-05-15</date><risdate>2015</risdate><volume>80</volume><issue>10</issue><spage>5125</spage><epage>5132</epage><pages>5125-5132</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet–Spengler reactions (86–92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25909585</pmid><doi>10.1021/acs.joc.5b00509</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Alkaloids - chemical synthesis Alkaloids - chemistry Benzylisoquinolines - chemistry Biological Products - chemical synthesis Biological Products - chemistry Catalysis Cyclization Ethylamines - chemistry Isoquinolines - chemistry Molecular Structure Organic Chemistry Phenomena Stereoisomerism Tetrahydroisoquinolines - chemical synthesis Tetrahydroisoquinolines - chemistry |
| title | Organocatalytic Enantioselective Pictet–Spengler Approach to Biologically Relevant 1‑Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids |
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