{"title":"(-)-鬼臼毒素的不对称全合成","authors":"Edward J. Bush, David W. Jones","doi":"10.1039/P19960000151","DOIUrl":null,"url":null,"abstract":"(–)-Podophyllotoxin of 98% optical purity has been synthesized in eight steps and in 15% overall yield. The key step, Diels–Alder addition of the o-quinonoid pyrone 2 [6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2-benzopyran-3-one] to the chiral dienophile 5 [5-(–)-menthyloxyfuran-2(5H)-one], proceeds with very high regio-, endo- and facial selectivity.","PeriodicalId":17267,"journal":{"name":"Journal of The Chemical Society-perkin Transactions 1","volume":"7 1","pages":"151-155"},"PeriodicalIF":0.0000,"publicationDate":"2010-08-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"47","resultStr":"{\"title\":\"Asymmetric total synthesis of (–)-podophyllotoxin\",\"authors\":\"Edward J. Bush, David W. Jones\",\"doi\":\"10.1039/P19960000151\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"(–)-Podophyllotoxin of 98% optical purity has been synthesized in eight steps and in 15% overall yield. The key step, Diels–Alder addition of the o-quinonoid pyrone 2 [6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2-benzopyran-3-one] to the chiral dienophile 5 [5-(–)-menthyloxyfuran-2(5H)-one], proceeds with very high regio-, endo- and facial selectivity.\",\"PeriodicalId\":17267,\"journal\":{\"name\":\"Journal of The Chemical Society-perkin Transactions 1\",\"volume\":\"7 1\",\"pages\":\"151-155\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2010-08-04\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"47\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of The Chemical Society-perkin Transactions 1\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1039/P19960000151\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of The Chemical Society-perkin Transactions 1","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1039/P19960000151","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
(–)-Podophyllotoxin of 98% optical purity has been synthesized in eight steps and in 15% overall yield. The key step, Diels–Alder addition of the o-quinonoid pyrone 2 [6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2-benzopyran-3-one] to the chiral dienophile 5 [5-(–)-menthyloxyfuran-2(5H)-one], proceeds with very high regio-, endo- and facial selectivity.
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