{"title":"钙化醇及其近亲。十四。去- ab -胆甾烷-8β，9α-二醇2{1β-[(1R)-1,5-二甲基己基]-7a - β-甲基-反式过氢茚-4β，5α-二醇}的全合成","authors":"I. J. Bolton, R. Harrison, B. Lythgoe","doi":"10.1039/J39710002950","DOIUrl":null,"url":null,"abstract":"In a new route to 1-substituted trans-3a,6,7,7a-tetrahydro-7a-methylindan-2-ones, a 1-monoester of 4-methyl-cyclohex-3-ene-1,trans-2-diol is subjected to two successive Claisen-type rearrangements to give, in a stereospecific manner, derivatives of 1-methylcyclohex-3-ene-1,trans-2-diacetic acid, which are then cyclised. Applied to the 1-benzoate (16) and methyl orthodihydrocitronellate (17), the method provides a direct synthesis of the 1,5-dimethylhexylindanone (20), and thence of the title diol (22), required for use in the total synthesis of tachysterol3 and precalciferol3.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"1 1","pages":"2950-2955"},"PeriodicalIF":0.0000,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"7","resultStr":"{\"title\":\"Calciferol and its relatives. Part XIV. Total synthesis of des-AB-cholestane-8β,9α-diol 2{1β-[(1R)-1,5-dimethylhexyl]-7aβ-methyl-trans-perhydroindane-4β,5α-diol}\",\"authors\":\"I. J. Bolton, R. Harrison, B. Lythgoe\",\"doi\":\"10.1039/J39710002950\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"In a new route to 1-substituted trans-3a,6,7,7a-tetrahydro-7a-methylindan-2-ones, a 1-monoester of 4-methyl-cyclohex-3-ene-1,trans-2-diol is subjected to two successive Claisen-type rearrangements to give, in a stereospecific manner, derivatives of 1-methylcyclohex-3-ene-1,trans-2-diacetic acid, which are then cyclised. Applied to the 1-benzoate (16) and methyl orthodihydrocitronellate (17), the method provides a direct synthesis of the 1,5-dimethylhexylindanone (20), and thence of the title diol (22), required for use in the total synthesis of tachysterol3 and precalciferol3.\",\"PeriodicalId\":17245,\"journal\":{\"name\":\"Journal of The Chemical Society C: Organic\",\"volume\":\"1 1\",\"pages\":\"2950-2955\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"1971-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"7\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of The Chemical Society C: Organic\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1039/J39710002950\",\"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 C: Organic","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1039/J39710002950","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Calciferol and its relatives. Part XIV. Total synthesis of des-AB-cholestane-8β,9α-diol 2{1β-[(1R)-1,5-dimethylhexyl]-7aβ-methyl-trans-perhydroindane-4β,5α-diol}
In a new route to 1-substituted trans-3a,6,7,7a-tetrahydro-7a-methylindan-2-ones, a 1-monoester of 4-methyl-cyclohex-3-ene-1,trans-2-diol is subjected to two successive Claisen-type rearrangements to give, in a stereospecific manner, derivatives of 1-methylcyclohex-3-ene-1,trans-2-diacetic acid, which are then cyclised. Applied to the 1-benzoate (16) and methyl orthodihydrocitronellate (17), the method provides a direct synthesis of the 1,5-dimethylhexylindanone (20), and thence of the title diol (22), required for use in the total synthesis of tachysterol3 and precalciferol3.
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