A Two-Directional Synthesis of (±)-Perhydrohistrionicotoxin
An entirely two-directional synthesis of (±)-perhydrohistrionicotoxin is presented, utilizing a tandem oxime formation/Michael addition/[3 + 2] cycloaddition as the key step. This approach also constitutes formal syntheses of (±)-histrionicotoxin and (±)-histrionicotoxin 235A.
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| Veröffentlicht in: | Journal of organic chemistry 2004-03, Vol.69 (5), p.1598-1602 |
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| container_end_page | 1602 |
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| container_issue | 5 |
| container_start_page | 1598 |
| container_title | Journal of organic chemistry |
| container_volume | 69 |
| creator | Stockman, Robert A Sinclair, Alex Arini, Louise G Szeto, Peter Hughes, David L |
| description | An entirely two-directional synthesis of (±)-perhydrohistrionicotoxin is presented, utilizing a tandem oxime formation/Michael addition/[3 + 2] cycloaddition as the key step. This approach also constitutes formal syntheses of (±)-histrionicotoxin and (±)-histrionicotoxin 235A. |
| doi_str_mv | 10.1021/jo035639a |
| format | Article |
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Antivenoms</subject><subject>Animals</subject><subject>Anura</subject><subject>Biological and medical sciences</subject><subject>Chemistry</subject><subject>Crystallography, X-Ray</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Skin - chemistry</subject><subject>Stereoisomerism</subject><subject>Toxicology</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0c1OAjEUBeDGaATRhS9g2GhkMdpO_2YSNwQVDQZJwLhsSqcTisMU2yHCY_kKPpklENiY2E0X_XLSey4A5wjeIBij26mFmDKcygNQRzSGEUshOQR1COM4wjHDNXDi_RSGQyk9BjVE0oRDxOrgrt0cfdno3jitKmNLWTSHq7KaaG980-bN65_vVjTQbrLKnJ0YX7mAjLKVXZryFBzlsvD6bHs3wNvjw6jzFL28dp877ZdIEk6rSBPOEkoymBGIcgJZrmDKxzmnEqdKEa2zJEYIYaLJOKeSpipBlGWpijMdjzVugKtN7tzZz4X2lZgZr3RRyFLbhRccsQRTBANsbaBy1nunczF3ZibdSiAo1lWJXVXBXmxDF-OZzvZy200Al1sgvZJF7mSpjN87FmJowv91lKIw3jov2rjQol7u3qX7EIxjTsVoMBS9925_0Es7or_PlcqHfy9cWI7_Y5Bfq-WYrg</recordid><startdate>20040305</startdate><enddate>20040305</enddate><creator>Stockman, Robert A</creator><creator>Sinclair, Alex</creator><creator>Arini, Louise G</creator><creator>Szeto, Peter</creator><creator>Hughes, David L</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><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>20040305</creationdate><title>A Two-Directional Synthesis of (±)-Perhydrohistrionicotoxin</title><author>Stockman, Robert A ; Sinclair, Alex ; Arini, Louise G ; Szeto, Peter ; Hughes, David L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a475t-e476854d0d401f406fc097bf75a39cc4eed8211134e4bf5a59c8156d9c2de2be3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Amphibian Venoms - chemical synthesis</topic><topic>Amphibian Venoms - chemistry</topic><topic>Amphibian Venoms - isolation & purification</topic><topic>Animal poisons toxicology. Antivenoms</topic><topic>Animals</topic><topic>Anura</topic><topic>Biological and medical sciences</topic><topic>Chemistry</topic><topic>Crystallography, X-Ray</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Skin - chemistry</topic><topic>Stereoisomerism</topic><topic>Toxicology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Stockman, Robert A</creatorcontrib><creatorcontrib>Sinclair, Alex</creatorcontrib><creatorcontrib>Arini, Louise G</creatorcontrib><creatorcontrib>Szeto, Peter</creatorcontrib><creatorcontrib>Hughes, David L</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><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>Stockman, Robert A</au><au>Sinclair, Alex</au><au>Arini, Louise G</au><au>Szeto, Peter</au><au>Hughes, David L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Two-Directional Synthesis of (±)-Perhydrohistrionicotoxin</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2004-03-05</date><risdate>2004</risdate><volume>69</volume><issue>5</issue><spage>1598</spage><epage>1602</epage><pages>1598-1602</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>An entirely two-directional synthesis of (±)-perhydrohistrionicotoxin is presented, utilizing a tandem oxime formation/Michael addition/[3 + 2] cycloaddition as the key step. This approach also constitutes formal syntheses of (±)-histrionicotoxin and (±)-histrionicotoxin 235A.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>14987016</pmid><doi>10.1021/jo035639a</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2004-03, Vol.69 (5), p.1598-1602 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Amphibian Venoms - chemical synthesis Amphibian Venoms - chemistry Amphibian Venoms - isolation & purification Animal poisons toxicology. Antivenoms Animals Anura Biological and medical sciences Chemistry Crystallography, X-Ray Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Medical sciences Models, Molecular Molecular Structure Organic chemistry Preparations and properties Skin - chemistry Stereoisomerism Toxicology |
| title | A Two-Directional Synthesis of (±)-Perhydrohistrionicotoxin |
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