Stability of alkoxy-substituted inden-2-ones and 6,7-dimethoxy-1,4-diphenyl-2,3-naphthoquinone

Bradshaw, David P.; Jones, David W.; Nongrum, F. M.

doi:10.1039/p19910000019

Cited by 8 publications

(2 citation statements)

References 5 publications

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“…We then tried to synthesize the other possible diastereomers starting from the synthetic intermediate 12 shown in Scheme . Selective oxidation of the secondary alcohol of 12 under Pfitzner–Moffart conditions proceeded with epimerization to give ketone 17 as a mixture of two diastereomers . Fortunately, comparable amounts of all the other three stereoisomers of the starting alcohol 12 were obtained by the reduction of this diastereomer mixture with NaBH 4 (Scheme ) .…”

Section: Figurementioning

confidence: 99%

“…Selectiveo xidation of the secondary alcoholo f12 under Pfitzner-Moffart conditions proceeded with epimerization to give ketone 17 as am ixture of two diastereomers. [12] Fortunately,c omparable amounts of all the other three stereoisomers of the startinga lcohol 12 were obtained by the reduction of this diastereomer mixture with NaBH 4 (Scheme 4). [13,14] These stereoisomers were separable by silica-gel chromatography and subsequenta minationr eactions were carried out independently.…”

Section: Total Synthesismentioning

confidence: 99%

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Total Synthesis of Proposed Structure of Yuremamine and All Diastereomers Using [3+2]‐Cycloaddition of Platinum‐Containing Azomethine Ylide

Ohyama

Uchida

Kusama

et al. 2015

Chemistry An Asian Journal

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Total synthesis of the proposed structure of yuremamine has been achieved for the first time based on the intermolecular [3+2]-cycloaddition reaction of the platinum-containing azomethine ylide. All the possible diastereomers of yuremamine were also synthesized via the common intermediate. Through these syntheses, it was confirmed that the proposed structure of yuremamine and the diastereomers differ from the natural product.

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Section: Figurementioning

confidence: 99%

Section: Total Synthesismentioning

confidence: 99%

Total Synthesis of Proposed Structure of Yuremamine and All Diastereomers Using [3+2]‐Cycloaddition of Platinum‐Containing Azomethine Ylide

Ohyama

Uchida

Kusama

et al. 2015

Chemistry An Asian Journal

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ChemInform Abstract: Stability of Alkoxy‐Substituted Inden‐2‐ones and 6,7‐Dimethoxy‐1,4‐ diphenyl‐2,3‐naphthoquinone.

1991

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Alkoxyallene‐Based LANCA Three‐Component Synthesis of 1,2‐Diketones, Quinoxalines, and Unique Isoindenone Dimers and a Computational Study of the Isoindenone Dimerization

et al. 2020

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A series of β‐alkoxy‐β‐ketoenamides was prepared by the well‐established LANCA three‐component reaction of lithiated 1‐(2‐trimethylsilylethoxy)‐substituted allenes, nitriles, and α,β‐unsaturated carboxylic acids. The α‐tert‐butyl‐substituted compounds were smoothly converted into the expected 1,2‐diketones by treatment with trifluoroacetic acid. A subsequent condensation of the 1,2‐diketones with o‐phenylenediamine provided the desired highly substituted quinoxalines in good overall yield. Surprisingly, the α‐phenyl‐substituted β‐alkoxy‐β‐ketoenamides investigated afford not only the expected 1,2‐diketones, but also pentacyclic compounds with an anti‐tricyclo[4.2.1.12,5]deca‐3,7‐diene‐9,10‐dione core. These interesting products are very likely the result of an isoindenone dimerization which was mechanistically studied with the support of DFT calculations. Under the strongly acidic reaction conditions, a stepwise reaction is likely leading to a protonated isoindenone as reactive intermediate. It may first form a van der Waals complex with a neutral isoindenone before the two regio‐ and diastereoselective ring forming steps occur. Interestingly, two neutral or two protonated isoindenones are also predicted to dimerize giving the observed pentacyclic product.||||||

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Stability of alkoxy-substituted inden-2-ones and 6,7-dimethoxy-1,4-diphenyl-2,3-naphthoquinone

Cited by 8 publications

References 5 publications

Total Synthesis of Proposed Structure of Yuremamine and All Diastereomers Using [3+2]‐Cycloaddition of Platinum‐Containing Azomethine Ylide

Total Synthesis of Proposed Structure of Yuremamine and All Diastereomers Using [3+2]‐Cycloaddition of Platinum‐Containing Azomethine Ylide

ChemInform Abstract: Stability of Alkoxy‐Substituted Inden‐2‐ones and 6,7‐Dimethoxy‐1,4‐ diphenyl‐2,3‐naphthoquinone.

Alkoxyallene‐Based LANCA Three‐Component Synthesis of 1,2‐Diketones, Quinoxalines, and Unique Isoindenone Dimers and a Computational Study of the Isoindenone Dimerization

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