Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/96086
Type: Artigo de periódico
Title: One-pot Preparation Of Quinolizidin-2-one And Indolizidin-7-one Ring Systems. Concise Total Synthesis Of (±)-myrtine, (±)-lasubine Ii, And (-)-indolizidine 223ab
Author: Pilli R.A.
Carlos Dias L.
Maldaner A.O.
Abstract: A 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.
Editor: 
Rights: fechado
Identifier DOI: 10.1021/jo00108a040
Address: http://www.scopus.com/inward/record.url?eid=2-s2.0-0028840773&partnerID=40&md5=397fda32f72f3e8c273e0623383b254d
Date Issue: 1995
Appears in Collections:Unicamp - Artigos e Outros Documentos

Files in This Item:
File Description SizeFormat 
2-s2.0-0028840773.pdf707.91 kBAdobe PDFView/Open


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.