One-pot Preparation Of Quinolizidin-2-one And Indolizidin-7-one Ring Systems. Concise Total Synthesis Of (±)-myrtine, (±)-lasubine Ii, And (-)-indolizidine 223ab

dc.creatorPilli R.A.
dc.creatorCarlos Dias L.
dc.creatorMaldaner A.O.
dc.date1995
dc.date2015-06-26T17:15:04Z
dc.date2015-11-26T14:21:19Z
dc.date2015-06-26T17:15:04Z
dc.date2015-11-26T14:21:19Z
dc.date.accessioned2018-03-28T21:23:04Z
dc.date.available2018-03-28T21:23:04Z
dc.identifier
dc.identifierJournal Of Organic Chemistry. , v. 60, n. 3, p. 717 - 722, 1995.
dc.identifier223263
dc.identifier10.1021/jo00108a040
dc.identifierhttp://www.scopus.com/inward/record.url?eid=2-s2.0-0028840773&partnerID=40&md5=397fda32f72f3e8c273e0623383b254d
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/96086
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/96086
dc.identifier2-s2.0-0028840773
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1244498
dc.descriptionA highly efficient approach to the quinolizidine alkaloids (±)-myrtine (4) and (±)-lasubine II (5) and to the indolizidine alkaloid (-)-indolizidine 223AB (6) is described. The preparation of quinolizidin-2-ones 4/4a and 11b/12b and indolizidin-7-ones 16/17 is based on the addition of 2-((trimethylsilyl)oxy) 1,3-dienes 2a,b and 2c to cyclic N-acyliminium ions 10 and 15, respectively. It encompasses five chemical transformations in the same pot yielding the axially oriented substituent at C-4 and C-5 as the major product in the quinolizidin-2-one and indolizidin-7-one systems, respectively. The thermodynamically more stable isomers 12b and 17 were obtained after basic treatment.
dc.description60
dc.description3
dc.description717
dc.description722
dc.languageen
dc.publisher
dc.relationJournal of Organic Chemistry
dc.rightsfechado
dc.sourceScopus
dc.titleOne-pot Preparation Of Quinolizidin-2-one And Indolizidin-7-one Ring Systems. Concise Total Synthesis Of (±)-myrtine, (±)-lasubine Ii, And (-)-indolizidine 223ab
dc.typeArtículos de revistas


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