{"title":"Stereoselective Synthesis of (R)-all-trans-13,14-Dihydroretinol and -Retinoic Acid","authors":"Paul Wienecke, Adriaan J. Minnaard","doi":"10.1021/acs.joc.4c03173","DOIUrl":null,"url":null,"abstract":"Vitamin A (or all-<i>trans</i>-retinol) metabolites are involved in a wide range of cellular processes. However, the investigation of their biological role is hampered due to their very limited availability. Herein we report a stereoselective total synthesis of the vitamin A metabolites (<i>R</i>)-all-<i>trans</i>-13,14-dihydroretinol and -retinoic acid, applying an <i>E</i>-selective HWE olefination and a Ru(II) catalyzed intramolecular 7-<i>endo</i>-<i>dig</i> hydrosilylation as the key steps.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"50 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c03173","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Vitamin A (or all-trans-retinol) metabolites are involved in a wide range of cellular processes. However, the investigation of their biological role is hampered due to their very limited availability. Herein we report a stereoselective total synthesis of the vitamin A metabolites (R)-all-trans-13,14-dihydroretinol and -retinoic acid, applying an E-selective HWE olefination and a Ru(II) catalyzed intramolecular 7-endo-dig hydrosilylation as the key steps.
期刊介绍：
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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