Design and Synthesis of Novel Propellanes by Using Claisen Rearrangement and Ring‐Closing Metathesis as the Key Steps

Kotha, Sambasivarao; Dipak, Mirtunjay Kumar

doi:10.1002/chem.200501366

Cited by 58 publications

(31 citation statements)

References 26 publications

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“…RCM strategy has also been extended to design new and annulated cage systems. Here, a novel route towards the synthesis of cage [4.4.2]propellane system 215 via a RCM was reported . In this regard, [4+2] cycloaddition followed by [2+2] cycloaddition sequence was employed to assemble the desired precursor 213 .…”

Section: Propellanesmentioning

confidence: 99%

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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Section: Propellanesmentioning

confidence: 99%

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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“…We demonstrated a new approach to assemble cage systems 68 starting with readily available hydroquinone ( 61 ). Here, a RCM strategy was employed as the crucial step to construct cage [4.4.2]propellane system 68 . To this end, hydroquinone ( 61 ) was transformed into diallyl product 62 .…”

Section: Applications Of the Claisen Rearrangement And Related Processesmentioning

confidence: 99%

Application of Claisen Rearrangement and Olefin Metathesis in Organic Synthesis

Kotha

Meshram

2018

Chemistry An Asian Journal

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Several new synthetic methods to diverse polycycles and heterocycles on the basis of [3,3]-sigmatropic rearrangement and ring-closing metathesis as key steps are summarized. In this regard, Claisen, aza-Claisen, and Overman rearrangements are used in combination with other popular reactions such as ring-closing metathesis, Suzuki coupling, Diels-Alder reaction, and retro-Diels-Alder reaction. To this end, we prepared polycycles (e.g., cyclophanes, cage molecules), heterocycles (e.g., oxepins, azapins), carbocycles, and spirocycles with the use of the above protocol.

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“…The title compound can be prepared according to Kushner (1971) via a Diels-Alder reaction of cyclopentadiene with either naphthaquinone followed by [2 + 2] photo-cycloaddition and hydrogenation or 1,2,3,4-tetrahydro-5,8-naphthoquinone followed by [2 + 2] photo-cycloaddition (Kotha & Dipak, 2006 8, 55.1, 49.7, 44.2, 43.7, 41.3, 22.8, 19.3. …”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Hexacyclo[7.5.1.0^1,6.0^6,13.0^8,12.0^10,14]pentadecane-7,15-dione

et al. 2016

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The structure of the title cage compound, C15H16O2, comprises eight fused rings,viz.one four-membered, four five-membered and three six-membered. One of the internal C—C bonds is unusually long for a cyclobutane bond length [1.607 (3) Å] and is comparable with the equivalent value of 1.598 (4) Å in the unsaturated homolog hexacyclo[7.4.2.01,9.03,7.04,14.06,15]pentadeca-10,12-diene-2,8-dione.

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Design and Synthesis of Novel Propellanes by Using Claisen Rearrangement and Ring‐Closing Metathesis as the Key Steps

Abstract: Novel hexacyclic caged compounds are prepared by a combination of Claisen rearrangement and ring-closing metathesis (RCM). Additionally, a Grignard reaction in conjugation with RCM produced intricate hexacyclic caged molecules.

Cited by 58 publications

References 26 publications

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

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

Application of Claisen Rearrangement and Olefin Metathesis in Organic Synthesis

Hexacyclo[7.5.1.0^1,6.0^6,13.0^8,12.0^10,14]pentadecane-7,15-dione

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Design and Synthesis of Novel Propellanes by Using Claisen Rearrangement and Ring‐Closing Metathesis as the Key Steps

Abstract: Novel hexacyclic caged compounds are prepared by a combination of Claisen rearrangement and ring-closing metathesis (RCM). Additionally, a Grignard reaction in conjugation with RCM produced intricate hexacyclic caged molecules.

Cited by 58 publications

References 26 publications

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

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

Application of Claisen Rearrangement and Olefin Metathesis in Organic Synthesis

Hexacyclo[7.5.1.01,6.06,13.08,12.010,14]pentadecane-7,15-dione

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Hexacyclo[7.5.1.0^1,6.0^6,13.0^8,12.0^10,14]pentadecane-7,15-dione