Indanes and indenes are among the most important carbocycles. Many indane and indene derivatives have shown important pharmacological activities, and the indane and indene nuclei are structural motifs present in several natural products of biological relevance. In spite of their importance, only a few reviews on their preparation methods have appeared so far in the literature, the most recent ones being published about ten years ago. The present Review is aimed at filling this gap, presenting some of the most important and innovative approaches to indanes and indenes that have been published in the course of the last ten years (coverage: from 2005 to May, 2015).

Recent Advances in the Synthesis of Indanes and Indenes

Fully complementary bimetallic catalysis has been identified as an increasingly powerful tool for molecular transformations, which was largely inspired by early examples of sequential catalytic transformations. Thus, energy-efficient one-pot reactions involving different metal catalysts orchestrated in concert constitute an attractive alternative to multi-step protocols, with major recent progress through the elegant ligand design in heterobimetallic catalysis as well as sustainable photo-induced C-H transformations, among others. This review provides a critical assessment of the state of the art in heterobimetallic catalysis for sustainable organic syntheses (SOS), highlighting key advances and representative examples until summer 2017.

Heteromultimetallic catalysis for sustainable organic syntheses.

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Handbook Of Metathesis

All pharmaceutical products contain organic molecules; the source may be a natural product or a fully synthetic molecule, or a combination of both. Thus, it follows that organic chemistry underpins both existing and upcoming pharmaceutical products. The reverse relationship has also affected organic synthesis, changing its landscape towards increasingly complex targets. This Review article sets out to give a concise appraisal of this symbiotic relationship between organic chemistry and drug discovery, along with a discussion of the design concepts and highlighting key milestones along the journey. In particular, criteria for a high-quality compound library design enabling efficient virtual navigation of chemical space, as well as rise and fall of concepts for its synthetic exploration (such as combinatorial chemistry; diversity-, biology-, lead-, or fragment-oriented syntheses; and DNA-encoded libraries) are critically surveyed.

The Symbiotic Relationship Between Drug Discovery and Organic Chemistry.

We describe diverse approaches to various dienes and their utilization in the Diels–Alder reaction to produce a variety of polycycles. The dienes covered here are prepared by simple alkylation reaction or via the Claisen rearrangement or by enyne metathesis of alkyne or enyne building blocks. Here, we have also included the Diels–Alder chemistry of dendralenes, a higher analog of cross-conjugated dienes. The present article is inclusive of o-xylylene derivatives that are generated in situ starting with benzosultine or benzosulfone derivatives. The Diels–Alder reaction of these dienes with various dienophiles gave diverse polycyclic systems and biologically important targets.

Diversity-Oriented Approaches to Polycyclics and Bioinspired Molecules via the Diels-Alder Strategy: Green Chemistry, Synthetic Economy, and Beyond.

A rapid and general approach for the synthesis of amino-substituted indanes and tetralins from readily available alkyne-derived allylic alcohols via consecutive multibond-forming tandem processes has been developed. In the first one-pot tandem process, a series of cyclic dienes were prepared using an Overman rearrangement under thermal conditions, followed by a ruthenium(II)-catalyzed ring closing enyne metathesis reaction. The resulting exo-dienes were then subjected to a second one-pot tandem process involving a highly regioselective Diels–Alder reaction with alkynes, quinones or nitriles and a subsequent oxidation step to give a diverse library of C-1 amino-substituted indanes and tetralins in good overall yields.

Synthesis of amino-substituted indanes and tetralins via consecutive multibond-forming tandem processes.

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

Discovery of a multi-bond forming, four-step tandem process: construction of drug-like polycyclic scaffolds.

Diastereoselective synthesis of highly substituted polycyclic scaffolds via a one-pot four-step tandem catalytic process

A highly efficient one-pot multistep process involving an asymmetric Pd(II)-catalyzed Overman rearrangement and a Ru(II)-catalyzed ring-closing metathesis reaction has been developed for the preparation of (R)- or (S)-aminocyclopenta-2-enes. The rapid strategy employed and the relatively mild conditions of the one-pot process allowed the multigram synthesis of the carbocycles in high enantiomeric excess (92% ee). The synthetic utility of these compounds was demonstrated by the stereoselective incorporation of hydroxyl groups, generating cis-4- and cis-5-aminocyclopenta-2-en-1-ols, important building blocks for medicinal chemistry.

Mark W. Grafton

Papers

Synthesis of amino-substituted indanes and tetralins via consecutive multibond-forming tandem processes.

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

Discovery of a multi-bond forming, four-step tandem process: construction of drug-like polycyclic scaffolds.

Diastereoselective synthesis of highly substituted polycyclic scaffolds via a one-pot four-step tandem catalytic process

Asymmetric synthesis of cis-aminocyclopentenols, building blocks for medicinal chemistry.