{"title":"全合成(+/-)-单分子胺I和(+/-)-吲哚吡啶195B的aza-[2,3]- witig重排。","authors":"P Somfai, T Jarevång, U M Lindström, A Svensson","doi":"10.3891/acta.chem.scand.51-1024","DOIUrl":null,"url":null,"abstract":"<p><p>A novel synthesis of (+/-)-monomorine I (1) and (+/-)-indolizidine 195B (2) is described in which the key step is the highly efficient aza-[2,3]-Wittig rearrangement of vinylaziridine 12 into tetrahydropyridine 13. Functional group manipulation then gave ketone 16 which could be converted into the target alkaloids by reductive amination (1:2 1.5:1).</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"51 10","pages":"1024-9"},"PeriodicalIF":0.0000,"publicationDate":"1997-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"16","resultStr":"{\"title\":\"Total synthesis of (+/-)-monomorine I and (+/-)-indolizidine 195B by an aza-[2,3]-Wittig rearrangement of a vinylaziridine.\",\"authors\":\"P Somfai, T Jarevång, U M Lindström, A Svensson\",\"doi\":\"10.3891/acta.chem.scand.51-1024\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>A novel synthesis of (+/-)-monomorine I (1) and (+/-)-indolizidine 195B (2) is described in which the key step is the highly efficient aza-[2,3]-Wittig rearrangement of vinylaziridine 12 into tetrahydropyridine 13. Functional group manipulation then gave ketone 16 which could be converted into the target alkaloids by reductive amination (1:2 1.5:1).</p>\",\"PeriodicalId\":76966,\"journal\":{\"name\":\"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)\",\"volume\":\"51 10\",\"pages\":\"1024-9\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"1997-10-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"16\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.3891/acta.chem.scand.51-1024\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.3891/acta.chem.scand.51-1024","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Total synthesis of (+/-)-monomorine I and (+/-)-indolizidine 195B by an aza-[2,3]-Wittig rearrangement of a vinylaziridine.
A novel synthesis of (+/-)-monomorine I (1) and (+/-)-indolizidine 195B (2) is described in which the key step is the highly efficient aza-[2,3]-Wittig rearrangement of vinylaziridine 12 into tetrahydropyridine 13. Functional group manipulation then gave ketone 16 which could be converted into the target alkaloids by reductive amination (1:2 1.5:1).
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