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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.
Rights: fechado
Identifier DOI: 10.1021/jo00108a040
Date Issue: 1995
Appears in Collections:Unicamp - Artigos e Outros Documentos

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