Diversity-Oriented Approach to Macrocyclic Cyclophane Derivatives by Suzuki–Miyaura Cross-Coupling and Olefin Metathesis as Key Steps

Kotha, Sambasivarao; Chavan, Arjun S.; Shaikh, Mobin M.

doi:10.1021/jo2020714

Cited by 62 publications

(23 citation statements)

References 107 publications

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“…Despite the fact that cyclophanes have been extensively synthesized and evaluated because of their unique physical and chemical properties, examples of the isolation and total synthesis of cyclophane-containing natural products are rare and challenging. This has attracted the interest of synthetic chemists in search of new and efficient strategies for syntheses with a reduced number of steps [45,46]. …”

Section: Introductionmentioning

confidence: 99%

Quinone and Hydroquinone Metabolites from the Ascidians of the Genus Aplidium

et al. 2014

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Ascidians of the genus Aplidium are recognized as an important source of chemical diversity and bioactive natural products. Among the compounds produced by this genus are non-nitrogenous metabolites, mainly prenylated quinones and hydroquinones. This review discusses the isolation, structural elucidation, and biological activities of quinones, hydroquinones, rossinones, longithorones, longithorols, floresolides, scabellones, conicaquinones, aplidinones, thiaplidiaquinones, and conithiaquinones. A compilation of the 13C-NMR spectral data of these compounds is also presented.

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Section: Introductionmentioning

confidence: 99%

Quinone and Hydroquinone Metabolites from the Ascidians of the Genus Aplidium

et al. 2014

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“…Along similar lines, we reported various macrocycles using RCM as a key step. In this context, the diallyl compound 22 obtained by SM coupling was treated with G‐II catalyst at 50 °C to produce the dimer 23 (30 %) along with monomer 24 (15 %).…”

Section: Cyclophanesmentioning

confidence: 61%

Design and Synthesis of Polycycles, Heterocycles, and Macrocycles via Strategic Utilization of Ring‐Closing Metathesis

Kotha

Meshram

Dommaraju

2018

The Chemical Record

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In this perspective, we summarize new synthetic approaches for the construction of various polycyclic compounds involving ring-closing metathesis as a key step. In this regard, we used ring-closing metathesis in combination with other popular reactions like Suzuki-Miyaura coupling, Claisen rearrangement, Fischer indolization, Grignard addition, Diels-Alder reaction, and [2+2] cycloaddition reaction etc. To this end, a variety of functional molecules such as α-amino acids, cyclophanes, heterocycles, propellanes, spirocycles, and macrocycles have been prepared. The strategies developed and the molecules prepared here play a key role in designing new materials and also act as lead compounds in drug design. The strategies and tactics developed here are useful to design polycycles, macrocycles, and heterocycles of diverse ring systems.

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“…Kotha and co-workers [ 145 ] have synthesized cyclophanes by using 1,3-indanedione using freshly prepared KF-Celite followed by SM cross-coupling reaction with an excess amount of allylboronic acid pinacol ester and afforded the required diallyl derivative 157 in good yield. Surprisingly, when the dialkyl compound 157 was subjected to RCM, instead of the monomer, the dimeric cyclophane 158 was obtained which was further subjected to hydrogenation to deliver the saturated cyclophane derivative 159 ( Scheme 24 ).…”

Section: Reviewmentioning

confidence: 99%

Selected synthetic strategies to cyclophanes

Kotha¹,

Shirbhate²,

Waghule³

2015

Beilstein J. Org. Chem.

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SummaryIn this review we cover various approaches to meta- and paracyclophanes involving popular reactions. Generally, we have included a strategy where the reaction was used for assembling the cyclophane skeleton for further functionalization. In several instances, after the cyclophane is made several popular reactions are used and these are not covered here. We included various natural products related to cyclophanes. To keep the length of the review at a manageable level the literature related to orthocyclophanes was not included.

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Diversity-Oriented Approach to Macrocyclic Cyclophane Derivatives by Suzuki–Miyaura Cross-Coupling and Olefin Metathesis as Key Steps

Abstract: Palladium-catalyzed Suzuki-Miyaura (SM) cross-coupling reaction with allylboronic acid pinacol ester and titanium assisted cross-metathesis (CM)/ring-closing metathesis (RCM) cascade has been used to synthesize macrocyclic cyclophane derivatives.

Cited by 62 publications

References 107 publications

Quinone and Hydroquinone Metabolites from the Ascidians of the Genus Aplidium

Quinone and Hydroquinone Metabolites from the Ascidians of the Genus Aplidium

Design and Synthesis of Polycycles, Heterocycles, and Macrocycles via Strategic Utilization of Ring‐Closing Metathesis

Selected synthetic strategies to cyclophanes

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