Mohadese Yaghoobi Anzabi , Piotr Cmoch , Roman Luboradzki , Zbigniew Pakulski
{"title":"从软木烟洗涤固体中分离的friedelanes的选择性转化。","authors":"Mohadese Yaghoobi Anzabi , Piotr Cmoch , Roman Luboradzki , Zbigniew Pakulski","doi":"10.1016/j.steroids.2023.109333","DOIUrl":null,"url":null,"abstract":"<div><p>Friedelin (<strong>1</strong>) and 3-acetoxyfriedel-3-en-2-one (<strong>4</strong>), commonly known as friedelane triterpenoids, have been isolated from cork smoker wash solids (also known as black wax) on a multi-gram scale. These compounds are valuable starting materials for the synthesis of new friedelane derivatives. Stereoselective reduction of friedelin by treatment with LiAlH<sub>4</sub>, sodium, or catalytic hydrogenation results in the formation of both isomers of friedelinol (<strong>5</strong> and <strong>7</strong>) in excellent yields. Similarly, the reduction of 3-acetoxyfriedel-3-en-2-one gave <em>epi</em><strong><em>-</em></strong>cerin (<strong>14</strong>) and a series of isomeric 2,3-diols or α-hydroxyketones. These transformations provide the most straightforward and convenient methods for the synthesis of A-ring functionalised friedelane derivatives using easily accessible starting materials.</p></div>","PeriodicalId":21997,"journal":{"name":"Steroids","volume":null,"pages":null},"PeriodicalIF":2.1000,"publicationDate":"2023-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0039128X23001617/pdfft?md5=192fb94cc430e286f0bf378a7701f389&pid=1-s2.0-S0039128X23001617-main.pdf","citationCount":"0","resultStr":"{\"title\":\"Selective transformations of friedelanes isolated from cork smoker wash solids\",\"authors\":\"Mohadese Yaghoobi Anzabi , Piotr Cmoch , Roman Luboradzki , Zbigniew Pakulski\",\"doi\":\"10.1016/j.steroids.2023.109333\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Friedelin (<strong>1</strong>) and 3-acetoxyfriedel-3-en-2-one (<strong>4</strong>), commonly known as friedelane triterpenoids, have been isolated from cork smoker wash solids (also known as black wax) on a multi-gram scale. These compounds are valuable starting materials for the synthesis of new friedelane derivatives. Stereoselective reduction of friedelin by treatment with LiAlH<sub>4</sub>, sodium, or catalytic hydrogenation results in the formation of both isomers of friedelinol (<strong>5</strong> and <strong>7</strong>) in excellent yields. Similarly, the reduction of 3-acetoxyfriedel-3-en-2-one gave <em>epi</em><strong><em>-</em></strong>cerin (<strong>14</strong>) and a series of isomeric 2,3-diols or α-hydroxyketones. These transformations provide the most straightforward and convenient methods for the synthesis of A-ring functionalised friedelane derivatives using easily accessible starting materials.</p></div>\",\"PeriodicalId\":21997,\"journal\":{\"name\":\"Steroids\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2023-11-07\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.sciencedirect.com/science/article/pii/S0039128X23001617/pdfft?md5=192fb94cc430e286f0bf378a7701f389&pid=1-s2.0-S0039128X23001617-main.pdf\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Steroids\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0039128X23001617\",\"RegionNum\":4,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Steroids","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0039128X23001617","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
Selective transformations of friedelanes isolated from cork smoker wash solids
Friedelin (1) and 3-acetoxyfriedel-3-en-2-one (4), commonly known as friedelane triterpenoids, have been isolated from cork smoker wash solids (also known as black wax) on a multi-gram scale. These compounds are valuable starting materials for the synthesis of new friedelane derivatives. Stereoselective reduction of friedelin by treatment with LiAlH4, sodium, or catalytic hydrogenation results in the formation of both isomers of friedelinol (5 and 7) in excellent yields. Similarly, the reduction of 3-acetoxyfriedel-3-en-2-one gave epi-cerin (14) and a series of isomeric 2,3-diols or α-hydroxyketones. These transformations provide the most straightforward and convenient methods for the synthesis of A-ring functionalised friedelane derivatives using easily accessible starting materials.
期刊介绍:
STEROIDS is an international research journal devoted to studies on all chemical and biological aspects of steroidal moieties. The journal focuses on both experimental and theoretical studies on the biology, chemistry, biosynthesis, metabolism, molecular biology, physiology and pharmacology of steroids and other molecules that target or regulate steroid receptors. Manuscripts presenting clinical research related to steroids, steroid drug development, comparative endocrinology of steroid hormones, investigations on the mechanism of steroid action and steroid chemistry are all appropriate for submission for peer review. STEROIDS publishes both original research and timely reviews. For details concerning the preparation of manuscripts see Instructions to Authors, which is published in each issue of the journal.