Abstract
Among the natural or designed products containing the cyclobutane moiety, amino acids and nucleosides are relevant. Some of these compounds are receiving much attention due to their biological properties as antibiotics, and antiviral or antitumoral agents. Synthetic approaches to these compounds are considered in this review, based on [2+2]- photocycloadditions or on the use of suitable precursors bearing the pre-formed cyclobutane ring. Absolute chirality is determined by the use of chiral precursors, i.e. terpenes, through chemoenzimatic resolutions, or by using chiral reagents and catalysts. Functionalization of the carbocyclic ring, a feature of crucial relevance, is the other synthetic challenge to be considered. More of ninety recent works are referred.
Keywords: cyclobutane containing amino acids, aminocyclobutanecarboxylic acid, peptidomimetics, transformations
Current Organic Chemistry
Title: Cyclobutane Biomolecules: Synthetic Approaches to Amino Acids, Peptides and Nucleosides
Volume: 9 Issue: 3
Author(s): Rosa M. Ortuno, Albertina G. Moglioni and Graciela Y. Moltrasio
Affiliation:
Keywords: cyclobutane containing amino acids, aminocyclobutanecarboxylic acid, peptidomimetics, transformations
Abstract: Among the natural or designed products containing the cyclobutane moiety, amino acids and nucleosides are relevant. Some of these compounds are receiving much attention due to their biological properties as antibiotics, and antiviral or antitumoral agents. Synthetic approaches to these compounds are considered in this review, based on [2+2]- photocycloadditions or on the use of suitable precursors bearing the pre-formed cyclobutane ring. Absolute chirality is determined by the use of chiral precursors, i.e. terpenes, through chemoenzimatic resolutions, or by using chiral reagents and catalysts. Functionalization of the carbocyclic ring, a feature of crucial relevance, is the other synthetic challenge to be considered. More of ninety recent works are referred.
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Cite this article as:
Ortuno M. Rosa, Moglioni G. Albertina and Moltrasio Y. Graciela, Cyclobutane Biomolecules: Synthetic Approaches to Amino Acids, Peptides and Nucleosides, Current Organic Chemistry 2005; 9 (3) . https://dx.doi.org/10.2174/1385272053369088
DOI https://dx.doi.org/10.2174/1385272053369088 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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