Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/195777
Type: Artigo de periódico
Title: Diastereoselective Synthesis Of Cularine Alkaloids Via Enium Ions And An Easy Entry To Isoquinolines By Aza-wittig Electrocyclic Ring Closure.
Author: Rodrigues, J Augusto R
Abramovitch, Rudolph A
de Sousa, Joana D F
Leiva, Genaro C
Abstract: In preliminary communications, we reported the diastereoselective synthesis of cularine and sarcocapnine via the intramolecular ring closure of nitrenium and oxenium ions, a new highly diastereoselective reductive methylation with (+)-8-phenylmenthyl chloroacetate followed by reduction with sodium borohydride, and a facile entry to the isoquinoline precursors by aza-Wittig electrocyclic ring closure. We now report the full details of the syntheses of (+)-O-demethylcularine, (+)-cularine, (+)-sarcocapnidine, (+)-sarcocapnine, and (+)-crassifoline and describe different methods of synthesis of their precursors.
Subject: Acetates
Alkaloids
Cations
Cyclization
Free Radicals
Isoquinolines
Methylation
Molecular Structure
Oxepins
Oxidation-reduction
Stereoisomerism
Temperature
Time Factors
Rights: fechado
Identifier DOI: 10.1021/jo030287t
Address: http://www.ncbi.nlm.nih.gov/pubmed/15104427
Date Issue: 2004
Appears in Collections:Unicamp - Artigos e Outros Documentos

Files in This Item:
File SizeFormat 
pmed_15104427.pdf289.89 kBAdobe PDFView/Open


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