Total synthesis of ()-pateamine A, a novel immunosuppressive agent from Mycale sp
A convergent synthesis of the unique thiazole-containing polyene bis-lactone pateamine A ( 1 ) isolated from the marine sponge Mycale sp is described. The synthesis features the ubiquitous Stille sp 2 sp 2 coupling reaction to elaborate the E,Z-diene macrolide core 23 and the all-E polyenamine side...
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Veröffentlicht in: | Canadian journal of chemistry 2004-02, Vol.82 (2), p.353-365 |
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container_title | Canadian journal of chemistry |
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creator | Pattenden, Gerald Critcher, Douglas J Remuiñán, Modesto |
description | A convergent synthesis of the unique thiazole-containing polyene bis-lactone pateamine A (
1
) isolated from the marine sponge Mycale sp is described. The synthesis features the ubiquitous Stille sp
2
sp
2
coupling reaction to elaborate the E,Z-diene macrolide core
23
and the all-E polyenamine side chain in the natural product. It also highlights the scope for enantiopure sulfinimine intermediates in the synthesis of chiral β-amino ester moieties in complex structures.Key words: pateamine A, immunosuppressive agent from marine sponge Mycale sp, total synthesis, novel 19-membered bis-lactone, thiazole metabolite, polyenamine, Stille reaction, sulfinimines, chiral β-amino esters. |
doi_str_mv | 10.1139/v03-199 |
format | Article |
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1
) isolated from the marine sponge Mycale sp is described. The synthesis features the ubiquitous Stille sp
2
sp
2
coupling reaction to elaborate the E,Z-diene macrolide core
23
and the all-E polyenamine side chain in the natural product. It also highlights the scope for enantiopure sulfinimine intermediates in the synthesis of chiral β-amino ester moieties in complex structures.Key words: pateamine A, immunosuppressive agent from marine sponge Mycale sp, total synthesis, novel 19-membered bis-lactone, thiazole metabolite, polyenamine, Stille reaction, sulfinimines, chiral β-amino esters.</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v03-199</identifier><language>eng</language><publisher>Ottawa, Canada: NRC Research Press</publisher><subject>Mycale</subject><ispartof>Canadian journal of chemistry, 2004-02, Vol.82 (2), p.353-365</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c378t-ecdf9478644ca810ecc82ec0a54b3dba4e1b23ebe9ced13a7b4359cb0816e8d43</citedby><cites>FETCH-LOGICAL-c378t-ecdf9478644ca810ecc82ec0a54b3dba4e1b23ebe9ced13a7b4359cb0816e8d43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,27928,27929</link.rule.ids></links><search><creatorcontrib>Pattenden, Gerald</creatorcontrib><creatorcontrib>Critcher, Douglas J</creatorcontrib><creatorcontrib>Remuiñán, Modesto</creatorcontrib><title>Total synthesis of ()-pateamine A, a novel immunosuppressive agent from Mycale sp</title><title>Canadian journal of chemistry</title><addtitle>Revue canadienne de chimie</addtitle><description>A convergent synthesis of the unique thiazole-containing polyene bis-lactone pateamine A (
1
) isolated from the marine sponge Mycale sp is described. The synthesis features the ubiquitous Stille sp
2
sp
2
coupling reaction to elaborate the E,Z-diene macrolide core
23
and the all-E polyenamine side chain in the natural product. It also highlights the scope for enantiopure sulfinimine intermediates in the synthesis of chiral β-amino ester moieties in complex structures.Key words: pateamine A, immunosuppressive agent from marine sponge Mycale sp, total synthesis, novel 19-membered bis-lactone, thiazole metabolite, polyenamine, Stille reaction, sulfinimines, chiral β-amino esters.</description><subject>Mycale</subject><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNqN0M1KxDAUhuEgCo6jeAtZ-YfVpEmnyXIY_IMRF47rkKanTqVtak47MDfiBXllVmbAleLqcODhW7yEHHN2xbnQ1ysmIq71DhlxqVgkYs13yYgxpiLJZLxPDhDfhjdlcTIizwvf2YriuumWgCVSX9Czz4_zqLUd2LpsgE4vqaWNX0FFy7ruG4992wZALFdA7Ss0HS2Cr-nj2tkKKLaHZK-wFcLR9o7Jy-3NYnYfzZ_uHmbTeeREqroIXF5omaqJlM4qzsA5FYNjNpGZyDMrgWexgAy0g5wLm2ZSJNplTPEJqFyKMTnd7LbBv_eAnalLdFBVtgHfo0nlJBYs5fF_JE9SPeE_0gWPGKAwbShrG9aGM_Pd1wx9zdB3kBcb2QQ31AAb3PIPfPI73iLT5oX4Aro1iaE</recordid><startdate>20040201</startdate><enddate>20040201</enddate><creator>Pattenden, Gerald</creator><creator>Critcher, Douglas J</creator><creator>Remuiñán, Modesto</creator><general>NRC Research Press</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7T5</scope><scope>H94</scope></search><sort><creationdate>20040201</creationdate><title>Total synthesis of ()-pateamine A, a novel immunosuppressive agent from Mycale sp</title><author>Pattenden, Gerald ; Critcher, Douglas J ; Remuiñán, Modesto</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c378t-ecdf9478644ca810ecc82ec0a54b3dba4e1b23ebe9ced13a7b4359cb0816e8d43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Mycale</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pattenden, Gerald</creatorcontrib><creatorcontrib>Critcher, Douglas J</creatorcontrib><creatorcontrib>Remuiñán, Modesto</creatorcontrib><collection>CrossRef</collection><collection>Immunology Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pattenden, Gerald</au><au>Critcher, Douglas J</au><au>Remuiñán, Modesto</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total synthesis of ()-pateamine A, a novel immunosuppressive agent from Mycale sp</atitle><jtitle>Canadian journal of chemistry</jtitle><addtitle>Revue canadienne de chimie</addtitle><date>2004-02-01</date><risdate>2004</risdate><volume>82</volume><issue>2</issue><spage>353</spage><epage>365</epage><pages>353-365</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><abstract>A convergent synthesis of the unique thiazole-containing polyene bis-lactone pateamine A (
1
) isolated from the marine sponge Mycale sp is described. The synthesis features the ubiquitous Stille sp
2
sp
2
coupling reaction to elaborate the E,Z-diene macrolide core
23
and the all-E polyenamine side chain in the natural product. It also highlights the scope for enantiopure sulfinimine intermediates in the synthesis of chiral β-amino ester moieties in complex structures.Key words: pateamine A, immunosuppressive agent from marine sponge Mycale sp, total synthesis, novel 19-membered bis-lactone, thiazole metabolite, polyenamine, Stille reaction, sulfinimines, chiral β-amino esters.</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v03-199</doi><tpages>13</tpages></addata></record> |
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language | eng |
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subjects | Mycale |
title | Total synthesis of ()-pateamine A, a novel immunosuppressive agent from Mycale sp |
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