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Synthesis 2014; 46(16): 2099-2121
DOI: 10.1055/s-0033-1341247
DOI: 10.1055/s-0033-1341247
review
Diversity-Oriented Asymmetric Synthesis
Further Information
Publication History
Received: 12 February 2014
Accepted after revision: 02 April 2014
Publication Date:
30 July 2014 (online)
Dedicated to Dr. Michael Harmata.
Abstract
The application of small molecules to modulate proteins by direct interactions has evolved as a powerful tool for the study of complex biological systems. Conventional genetic approaches have examined biological systems by generating random mutations which were then screened in search of a precise cellular phenotype. Analogous to the genetic approach, large random collections of small molecules can be used to elucidate the roles of specific proteins in many biological pathways. The crux of this ‘chemical genetic’ approach is the design and synthesis of libraries of compounds which span large tracts of biologically relevant chemical space. Diversity-oriented asymmetric synthesis (DOAS) is an exceptional methodology for preparing structurally and stereochemically diverse small molecule libraries which show a greater variety not only in their physiochemical properties but also in their biological activities. Herein, we describe some of the most effective strategies that have been used in asymmetric diversity-oriented synthesis library design and preparation.
1 Introduction
2 Philosophy of DOAS
3 Stoichiometric Reactions
3.1 DOAS with Chiral Auxiliaries
3.2 DOAS with Chiral Templates
3.3 DOAS with Chiral ‘Linchpins’
3.4 DOAS from Natural Products via a Ring-Distortion Strategy
3.5 DOAS via Chiral Reactions
4 DOAS towards Peptidomimetics
5 Catalytic Reactions
6 Conclusion
-
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For reductive cleavage, see:
For oxidative cleavage, see:
For hydrolysis, see:
For epoxides, see:
For reviews, see:
For reviews, see:
For an extensive list of biologically active sultams, as well as classical and transition-metal-catalyzed cyclization strategies to obtain sultams, see: