{"title":"20-羟基蜕皮酮和后睾酮2-酯和二氧烷衍生物的化学选择性合成","authors":"R. G. Savchenko, L. V. Parfenova","doi":"10.1007/s10600-025-04737-9","DOIUrl":null,"url":null,"abstract":"<p>Chemoselective approaches to the synthesis of ester and cyclic acetal derivatives of ecdysteroids with 5-bromovaleric and lipoic acids and aromatic heterocyclic aldehydes were proposed. Chemoselective formation of 2-monoester derivatives (compounds <b>4</b>–<b>7</b>) or dioxolane adducts (compounds <b>8</b>–<b>10</b>) occurred during condensation of an ecdysteroid with an acid or aldehyde. Compound <b>8</b>, which was prepared by acid-catalyzed condensation of 20-hydroxyecdysone with furfuraldehyde, was an analog of the phytoecdysteroid serfurosterone A, which was isolated from the plant Achyranthes bidentata.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 4","pages":"686 - 691"},"PeriodicalIF":0.9000,"publicationDate":"2025-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Chemoselective Synthesis of 2-Ester and Dioxolane Derivatives of 20-Hydroxyecdysone and Poststerone\",\"authors\":\"R. G. Savchenko, L. V. Parfenova\",\"doi\":\"10.1007/s10600-025-04737-9\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>Chemoselective approaches to the synthesis of ester and cyclic acetal derivatives of ecdysteroids with 5-bromovaleric and lipoic acids and aromatic heterocyclic aldehydes were proposed. Chemoselective formation of 2-monoester derivatives (compounds <b>4</b>–<b>7</b>) or dioxolane adducts (compounds <b>8</b>–<b>10</b>) occurred during condensation of an ecdysteroid with an acid or aldehyde. Compound <b>8</b>, which was prepared by acid-catalyzed condensation of 20-hydroxyecdysone with furfuraldehyde, was an analog of the phytoecdysteroid serfurosterone A, which was isolated from the plant Achyranthes bidentata.</p>\",\"PeriodicalId\":514,\"journal\":{\"name\":\"Chemistry of Natural Compounds\",\"volume\":\"61 4\",\"pages\":\"686 - 691\"},\"PeriodicalIF\":0.9000,\"publicationDate\":\"2025-07-22\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemistry of Natural Compounds\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s10600-025-04737-9\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry of Natural Compounds","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s10600-025-04737-9","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Chemoselective Synthesis of 2-Ester and Dioxolane Derivatives of 20-Hydroxyecdysone and Poststerone
Chemoselective approaches to the synthesis of ester and cyclic acetal derivatives of ecdysteroids with 5-bromovaleric and lipoic acids and aromatic heterocyclic aldehydes were proposed. Chemoselective formation of 2-monoester derivatives (compounds 4–7) or dioxolane adducts (compounds 8–10) occurred during condensation of an ecdysteroid with an acid or aldehyde. Compound 8, which was prepared by acid-catalyzed condensation of 20-hydroxyecdysone with furfuraldehyde, was an analog of the phytoecdysteroid serfurosterone A, which was isolated from the plant Achyranthes bidentata.
期刊介绍:
Chemistry of Natural Compounds publishes reviews and general articles about the structure of different classes of natural compounds, the chemical characteristics of botanical families, genus, and species, to establish the comparative laws and connection between physiological activity and the structure of substances.