Electrolytic Macrocyclizations: Scalable Synthesis of a Diazonamide-Based Drug Development Candidate
An electrochemical method to synthesize the core macrolactam of diazonamides is described. Large ring‐forming dehydrogenation is initiated by anodic oxidation at a graphite surface. The reaction requires no tailoring of the substrate and occurs at ambient temperature in aqueous DMF in an undivided c...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2015-04, Vol.54 (16), p.4818-4822 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Ding, Hui DeRoy, Patrick L. Perreault, Christian Larivée, Alexandre Siddiqui, Arshad Caldwell, Charles G. Harran, Susan Harran, Patrick G. |
| description | An electrochemical method to synthesize the core macrolactam of diazonamides is described. Large ring‐forming dehydrogenation is initiated by anodic oxidation at a graphite surface. The reaction requires no tailoring of the substrate and occurs at ambient temperature in aqueous DMF in an undivided cell open to air. This unique chemistry has enabled a concise, scalable preparation of DZ‐2384; a refined analog of diazonamide A slated for clinical development as a cancer therapeutic.
Electrifying chemistry! The core macrolactam of diazonamides can be synthesized electrochemically. This large ring forming dehydrogenation has enabled a concise preparation of DZ‐2384, a refined analogue of diazonamide A slated for clinical development as a cancer therapeutic. |
| doi_str_mv | 10.1002/anie.201411663 |
| format | Article |
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Electrifying chemistry! The core macrolactam of diazonamides can be synthesized electrochemically. This large ring forming dehydrogenation has enabled a concise preparation of DZ‐2384, a refined analogue of diazonamide A slated for clinical development as a cancer therapeutic.</description><subject>Ambient temperature</subject><subject>Amides - chemical synthesis</subject><subject>Amides - chemistry</subject><subject>Analogue</subject><subject>anodic oxidation</subject><subject>Anodizing</subject><subject>Azo Compounds - chemistry</subject><subject>Cancer</subject><subject>Crystallography, X-Ray</subject><subject>Cyclization</subject><subject>Dehydrogenation</subject><subject>Electrolytic cells</subject><subject>electrosynthesis</subject><subject>Forming</subject><subject>Graphite</subject><subject>Graphite - chemistry</subject><subject>Lactams, Macrocyclic - chemical synthesis</subject><subject>Lactams, Macrocyclic - chemistry</subject><subject>macrocycles</subject><subject>Macrocyclic compounds</subject><subject>Molecular Conformation</subject><subject>natural products</subject><subject>oxazoles</subject><subject>Oxazoles - chemical synthesis</subject><subject>Oxazoles - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Pharmaceutical Preparations - chemistry</subject><subject>Surface Properties</subject><subject>Synthesis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0U1v1DAQBmALgWgpXDmiSFy4ZPHY8Ue4tbvLUqksh4Iq9WLNJhNwcZIlTmjTX09WW1aIS0-ewzOv5HkZew18BpyL99h4mgkOGYDW8gk7BiUglcbIp9OcSZkaq-CIvYjxZvLWcv2cHQllRM65PWblMlDRd20Ye18kn7Ho2mIsgr_H3rdN_JBcFhhwEyi5HJv-B0Ufk7ZKMFl4vG8brH1J6RlGKpNFN3xPFvSbQrutqemTOTalL7Gnl-xZhSHSq4f3hH37uPw6_5RefFmdz08v0kKDkSkJm2uSeqMVlJaqHIWoSFk0ljI0ukKV5yBUJcjKCkWWWysLBXlWwaY0JE_Yu33utmt_DRR7V_tYUAjYUDtEB4YDF0oY8TjVRnCrJMiJvv2P3rRD10wf2SkuAKZjTmq2V9MFY-yoctvO19iNDrjbVeV2VblDVdPCm4fYYVNTeeB_u5lAvge3PtD4SJw7XZ8v_w1P97s-9nR32MXup9NGGuWu1iunM76-ul5du7n8A5oLrl0</recordid><startdate>20150413</startdate><enddate>20150413</enddate><creator>Ding, Hui</creator><creator>DeRoy, Patrick L.</creator><creator>Perreault, Christian</creator><creator>Larivée, Alexandre</creator><creator>Siddiqui, Arshad</creator><creator>Caldwell, Charles G.</creator><creator>Harran, Susan</creator><creator>Harran, Patrick G.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20150413</creationdate><title>Electrolytic Macrocyclizations: Scalable Synthesis of a Diazonamide-Based Drug Development Candidate</title><author>Ding, Hui ; 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Chem. Int. Ed</addtitle><date>2015-04-13</date><risdate>2015</risdate><volume>54</volume><issue>16</issue><spage>4818</spage><epage>4822</epage><pages>4818-4822</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>An electrochemical method to synthesize the core macrolactam of diazonamides is described. Large ring‐forming dehydrogenation is initiated by anodic oxidation at a graphite surface. The reaction requires no tailoring of the substrate and occurs at ambient temperature in aqueous DMF in an undivided cell open to air. This unique chemistry has enabled a concise, scalable preparation of DZ‐2384; a refined analog of diazonamide A slated for clinical development as a cancer therapeutic.
Electrifying chemistry! The core macrolactam of diazonamides can be synthesized electrochemically. This large ring forming dehydrogenation has enabled a concise preparation of DZ‐2384, a refined analogue of diazonamide A slated for clinical development as a cancer therapeutic.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25729008</pmid><doi>10.1002/anie.201411663</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | Ambient temperature Amides - chemical synthesis Amides - chemistry Analogue anodic oxidation Anodizing Azo Compounds - chemistry Cancer Crystallography, X-Ray Cyclization Dehydrogenation Electrolytic cells electrosynthesis Forming Graphite Graphite - chemistry Lactams, Macrocyclic - chemical synthesis Lactams, Macrocyclic - chemistry macrocycles Macrocyclic compounds Molecular Conformation natural products oxazoles Oxazoles - chemical synthesis Oxazoles - chemistry Oxidation-Reduction Pharmaceutical Preparations - chemistry Surface Properties Synthesis |
| title | Electrolytic Macrocyclizations: Scalable Synthesis of a Diazonamide-Based Drug Development Candidate |
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