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

被引:33
作者
Calder, Ewen D. D. [1 ]
Grafton, Mark W. [1 ]
Sutherland, Andrew [1 ]
机构
[1] Univ Glasgow, Sch Chem, WestCHEM, Glasgow G12 8QQ, Lanark, Scotland
基金
英国工程与自然科学研究理事会;
关键词
Overman rearrangement; metathesis; Diels-Alder reaction; catalysis; transition metals; multistep reaction; AZA-CLAISEN REARRANGEMENT; CATALYTIC ASYMMETRIC REARRANGEMENT; HIGH-YIELDING SYNTHESIS; ORGANIC-SYNTHESIS; ALLYLIC ALCOHOLS; STEREOSELECTIVE-SYNTHESIS; DIRECTED DIHYDROXYLATION; INHIBITOR (-)-OSELTAMIVIR; ANTINEOPLASTIC AGENTS; HETEROCYCLE SYNTHESIS;
D O I
10.1055/s-0033-1340683
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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
引用
收藏
页码:1068 / 1080
页数:13
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