4.4 Article

One-Pot Multi-Reaction Processes: Synthesis of Natural Products and Drug-Like Scaffolds

Journal

SYNLETT
Volume 25, Issue 8, Pages 1068-1080

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1340683

Keywords

Overman rearrangement; metathesis; Diels-Alder reaction; catalysis; transition metals; multistep reaction

Funding

  1. University of Glasgow
  2. EPSRC (DTA award)
  3. Schering-Plough Corporation
  4. Engineering and Physical Sciences Research Council [1097440] Funding Source: researchfish

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One-pot multi-reaction processes involving Overman rearrangements, metathesis cyclizations, and Diels-Alder reactions have been developed for the rapid and efficient synthesis of amino-substituted carbocyclic and heterocyclic compounds. This account describes the development and optimization of these processes, as well as their applications in the synthesis of natural products and drug-like scaffolds. 1 Introduction 2 A One-Pot Overman Rearrangement and Ring-Closing Metathesis Reaction 2.1 Scope and Limitations 2.2 Applications of the One-Pot Two-Step Process 2.3 A Directed Overman Rearrangement and Ring-Closing Metathesis Reaction Process 3 A One-Pot Three-Step Ruthenium(II) Tandem Catalytic Process 3.1 Development and Scope 3.2 A Microwave-Mediated One-Pot Three-Step Process 4 A One-Pot Three-Step Process Involving a Ring-Closing Enyne Metathesis and a Diels-Alder Reaction 4.1 Synthesis of Substrates 4.2 An Unexpected Hydrogen-Bonding-Directed Diels-Alder Reaction 4.3 Application of the Synthesis for C1-Amino-Substituted Indanes and Tetralins 4.4 Development of a Two-Pot Reaction Process 5 Conclusions

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