Synthesis of Pentahydroxylated Pyrrolizidines and Indolizidines

1,3-Dipolar cycloaddition reaction of nitrone 7 and chemo-enzymatically obtained alkenediols 12 and 13 has been used in the synthesis of pentahydroxylated pyrrolizidines (8 and 10) and indolizidines (9 and 11). The pyrrolizidinic and indolizidinic skeletons were built after internal n-alkylation of...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-08, Vol.74 (15), p.5679-5682
Main Authors: Tamayo, Juan A, Franco, Francisco, Lo Re, Daniele, Sánchez-Cantalejo, Fernando
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Indolizidines - chemical synthesis
Indolizidines - chemistry
Molecular Conformation
Organic chemistry
Preparations and properties
Pyrrolizidine Alkaloids - chemical synthesis
Pyrrolizidine Alkaloids - chemistry
Stereoisomerism
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Summary:1,3-Dipolar cycloaddition reaction of nitrone 7 and chemo-enzymatically obtained alkenediols 12 and 13 has been used in the synthesis of pentahydroxylated pyrrolizidines (8 and 10) and indolizidines (9 and 11). The pyrrolizidinic and indolizidinic skeletons were built after internal n-alkylation of the suitably functionalized pyrroloisoxazolidine intermediates obtained by the necessary protecting group manipulations. This method expands the scope of cycloaddition reactions in the synthesis of new and highly polyhydroxylated sugar-like alkaloids.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo900801c