Convergent, Stereoselective Synthesis of the GHIJ Fragment of Brevetoxin A
A stereoselective synthesis of the GHIJ fragment of brevetoxin A utilizing a convergent assembly strategy is described. Glycolate alkylation, ring-closing metathesis, and Hosomi−Sakurai reactions were central operations in the construction of the G ring and J ring subunits, which were united through...
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| Veröffentlicht in: | Organic letters 2006-01, Vol.8 (1), p.159-162 |
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| container_title | Organic letters |
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| creator | Crimmins, Michael T Zuccarello, J. Lucas Cleary, Pamela A Parrish, Jonathan D |
| description | A stereoselective synthesis of the GHIJ fragment of brevetoxin A utilizing a convergent assembly strategy is described. Glycolate alkylation, ring-closing metathesis, and Hosomi−Sakurai reactions were central operations in the construction of the G ring and J ring subunits, which were united through a Horner−Wadsworth−Emmons coupling. Subsequent dehydrative cyclization produced an endocyclic enol ether that was further elaborated to the tetracyclic GHIJ fragment of brevetoxin A. |
| doi_str_mv | 10.1021/ol0526625 |
| format | Article |
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Lucas</creatorcontrib><creatorcontrib>Cleary, Pamela A</creatorcontrib><creatorcontrib>Parrish, Jonathan D</creatorcontrib><title>Convergent, Stereoselective Synthesis of the GHIJ Fragment of Brevetoxin A</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A stereoselective synthesis of the GHIJ fragment of brevetoxin A utilizing a convergent assembly strategy is described. Glycolate alkylation, ring-closing metathesis, and Hosomi−Sakurai reactions were central operations in the construction of the G ring and J ring subunits, which were united through a Horner−Wadsworth−Emmons coupling. Subsequent dehydrative cyclization produced an endocyclic enol ether that was further elaborated to the tetracyclic GHIJ fragment of brevetoxin A.</description><subject>Marine Toxins - chemical synthesis</subject><subject>Marine Toxins - chemistry</subject><subject>Molecular Structure</subject><subject>Oxocins - chemical synthesis</subject><subject>Oxocins - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtOwzAURC0EoqWw4AeQNyyQCPjROPayRPSlSiwK68hxbkqqNq7sNKJ_j6tUZcPqzh0djUaD0D0lL5Qw-mo3JGZCsPgC9WnMeJSE__KsBemhG-_XhNDgqGvUo4JLGivWR_PU1i24FdTNM1424MB62IBpqhbw8lA33-Arj22Jg8KT6WyOx06vtoE_mm8OWmjsT1Xj0S26KvXGw93pDtDX-P0znUaLj8ksHS0izRPVRAK45FoOTV4mHEojuBoyEye51CKRkhVEaRAFzYtCUS058Bh0bhTkckgLEHyAnrpc46z3Dsps56qtdoeMkuy4R3beI7APHbvb51so_sjTAAF47ABtfLa2e1eH6v8E_QIT_WaJ</recordid><startdate>20060105</startdate><enddate>20060105</enddate><creator>Crimmins, Michael T</creator><creator>Zuccarello, J. 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Lucas ; Cleary, Pamela A ; Parrish, Jonathan D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-6e383a84cbf73efc63942c57b8a67882d09ae6d1bdd91a83e35eabc9eb841de63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Marine Toxins - chemical synthesis</topic><topic>Marine Toxins - chemistry</topic><topic>Molecular Structure</topic><topic>Oxocins - chemical synthesis</topic><topic>Oxocins - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Crimmins, Michael T</creatorcontrib><creatorcontrib>Zuccarello, J. 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| ispartof | Organic letters, 2006-01, Vol.8 (1), p.159-162 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_crossref_primary_10_1021_ol0526625 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Marine Toxins - chemical synthesis Marine Toxins - chemistry Molecular Structure Oxocins - chemical synthesis Oxocins - chemistry Stereoisomerism |
| title | Convergent, Stereoselective Synthesis of the GHIJ Fragment of Brevetoxin A |
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