Diastereoselective Synthesis of Cularine Alkaloids via Enium Ions and an Easy Entry to Isoquinolines by Aza-Wittig Electrocyclic Ring Closure

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 b...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-04, Vol.69 (9), p.2920-2928
Main Authors: Rodrigues, J. Augusto R, Abramovitch, Rudolph A, de Sousa, Joana D. F, Leiva, Genaro C
Format: Article
Language:English
Subjects:
Acetates - chemistry
Alkaloids - chemical synthesis
Cations - chemistry
Chemistry
Cyclization
Exact sciences and technology
Free Radicals - chemistry
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Isoquinolines - chemical synthesis
Methylation
Molecular Structure
Organic chemistry
Oxepins - chemical synthesis
Oxidation-Reduction
Preparations and properties
Stereoisomerism
Temperature
Time Factors
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo030287t