Synthesis of Natural Products Containing Medium‐Size Oxygen Heterocycles by Ring‐Closing Alkene Metathesis

Rainier, Jon D.

doi:10.1002/9783527629626.ch3

Cited by 16 publications

(6 citation statements)

References 91 publications

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“…Medium-ring-sized oxacycle synthesis has greatly advanced with the advent of the powerful ring-closing metathesis reaction . We, and others, have earlier demonstrated the efficacy of a combined Claisen rearrangement-ring closing metathesis sequence for the synthesis of benz-annulated oxepine derivatives.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Preliminary Biophysical and Cellular Evaluation of Some Ring-Enlarged Analogues of the Anti-Tumor Plant Alkaloid Acronycine

et al. 2019

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Three oxepinoacridine analogues of the important anti-cancer pyranoacridine natural product acronycine have been synthesized using a combined Claisen rearrangement ring-closing metathesis sequence as key steps to install the oxacyclic ring. Preliminary biophysical studies of these proposed oxepino analogues revealed that they interact with ct-DNA in a manner similar to the pyranoacridones but not possibly as intercalators. Cellular evaluations of these analogues in two human leukemic cell lines have also been carried out. These studies indicate that the ring-enlarged analogues have somewhat lower activity than the naturally occurring ones in the cell lines studied.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Preliminary Biophysical and Cellular Evaluation of Some Ring-Enlarged Analogues of the Anti-Tumor Plant Alkaloid Acronycine

et al. 2019

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“…These features make them quite useful especially for the total synthesis of natural products . Recently, gem -di(iodozincio)methanes have been shown to be useful reagents for methylenation and ring-closing metathesis cascades of olefinic esters, 1,4-addition to enones, nickel-catalyzed carbozincation of alkynes, and palladium-catalyzed sequential cross-coupling reactions …”

mentioning

confidence: 99%

Isolation and Structural Characterization ofGeminalDi(iodozincio)methane Complexes Stabilized with Nitrogen Ligands

et al. 2014

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Treatment of gem-di(iodozincio)methane with pyridine or diamine derivatives resulted in the isolation of a storable gem-di(iodozincio)methane species. Use of the sterically bulky bipyridine ligand gave a gem-di(iodozincio)methane complex, which allowed the first X-ray structural analysis of such species. This work represents a rare example of the isolation of an organometallic reactive species in Schlenk equilibrium and thus provides new insight into the design of efficient and storable organometallic reagents. The isolated gem-di(iodozincio)methane complexes serve as effective methylene dianion synthons for olefination of carbonyl compounds.

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“…It was dried over anhydrous Na 2 SO 4 and filtered. The filtrate was concentrated in vacuo to leave a crude mass that was purified by column chromatography over silica gel (100-200 mesh) using AcOEt/PE 1 : 9 as eluent to give 16 as colorless viscous liquid (2.190 (17). To a stirred solution of 16 (0.500 g, 1.26 mmol) in anhydrous toluene (20 mL), GÀ I (1 mol-%) was added under argon atmosphere.…”

Section: N-[4-methoxy-26-di(prop-2-en-1-yl)phenyl]mentioning

confidence: 99%

“…[2 -6] Recent progress in various metal-catalyzed ring-forming reactions has facilitated access to these classically otherwise difficult-to-make ring systems. [7][8][9][10][11][12][13][14] In particular, olefin-metathesis mediated transformations, [15][16][17][18][19][20][21][22][23][24][25][26][27][28] either in tandem or in sequence with other named and unnamed reactions, [29,30] have provided rapid access to several structurally embellished entities accommodating the core ring systems. However, comparatively less attention has been paid to develop synthetic methodologies that simultaneously address incorporation of functionalities within the core ring system.…”

Section: Introductionmentioning

confidence: 99%

Sequential Two‐Fold Claisen Rearrangement, One‐Pot Ring‐Closing Metathesis and Cross‐Metathesis as a Route to Substituted Benzo[b]azepine‐2‐one, Benzo[b]azepine and Benzo[b]oxepine Derivatives

Chattopadhyay

Mandal

Banerjee

et al. 2021

Helvetica Chimica Acta

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A synthetic protocol involving sequential use of three atom-economic processes viz. Claisen rearrangement, ring-closing metathesis and cross metathesis has been developed to access 7-substituted benzo[b]azepine and benzo[b]oxepine derivatives starting from appropriate aniline or phenol in good overall yield. A one-pot RCM-CM protocol has also been developed for the synthesis of benzazepine and benzoxepine derivatives.

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Synthesis of Natural Products Containing Medium‐Size Oxygen Heterocycles by Ring‐Closing Alkene Metathesis

Cited by 16 publications

References 91 publications

Synthesis and Preliminary Biophysical and Cellular Evaluation of Some Ring-Enlarged Analogues of the Anti-Tumor Plant Alkaloid Acronycine

Synthesis and Preliminary Biophysical and Cellular Evaluation of Some Ring-Enlarged Analogues of the Anti-Tumor Plant Alkaloid Acronycine

Isolation and Structural Characterization ofGeminalDi(iodozincio)methane Complexes Stabilized with Nitrogen Ligands

Sequential Two‐Fold Claisen Rearrangement, One‐Pot Ring‐Closing Metathesis and Cross‐Metathesis as a Route to Substituted Benzo[b]azepine‐2‐one, Benzo[b]azepine and Benzo[b]oxepine Derivatives

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