{"title":"Streamlined transformations of bicyclic enal intermediate – formal synthesis of Δ12-Prostaglandin J3","authors":"","doi":"10.1016/j.tetlet.2024.155176","DOIUrl":null,"url":null,"abstract":"<div><p>Herein we report improved shorter and practical synthesis of known enone-ester intermediate <strong>12</strong> as a gateway to anticancer Δ<sup>12</sup>-Prostaglandin J<sub>3</sub>. Several one-pot methods were developed to synthesize azide <strong>5</strong> directly from enal <strong>1</strong>, ene-carbamate <strong>7</strong> directly from lactone-acid <strong>4</strong> and enone-acid <strong>11</strong> directly from azide <strong>5</strong>. The step count (from 12 to 8 steps) improvements achieved makes this formal synthesis of Δ<sup>12</sup>-Prostaglandin J<sub>3</sub> one of the shortest.</p></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924002715","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Herein we report improved shorter and practical synthesis of known enone-ester intermediate 12 as a gateway to anticancer Δ12-Prostaglandin J3. Several one-pot methods were developed to synthesize azide 5 directly from enal 1, ene-carbamate 7 directly from lactone-acid 4 and enone-acid 11 directly from azide 5. The step count (from 12 to 8 steps) improvements achieved makes this formal synthesis of Δ12-Prostaglandin J3 one of the shortest.
期刊介绍：
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
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