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

Ewen D. D. Calder; Mark W. Grafton; Andrew Sutherland

doi:10.1055/s-0033-1340683

Synlett, Table of Contents

Synlett 2014; 25(08): 1068-1080
DOI: 10.1055/s-0033-1340683

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

Ewen D. D. Calder

WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, UK Fax: +44(141)3304888 Email: Andrew.Sutherland@glasgow.ac.uk

,

Mark W. Grafton

WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, UK Fax: +44(141)3304888 Email: Andrew.Sutherland@glasgow.ac.uk

,

Andrew Sutherland*

WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, UK Fax: +44(141)3304888 Email: Andrew.Sutherland@glasgow.ac.uk

› Author Affiliations

Abstract

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Abstract

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

Key words

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

Full Text

References

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