Synthesis of Some Spiro-Isoxazolidine-3,5-Diones

Reddy, D. Bhaskar; Padmavathi, V.; Seenaiah, B.; Reddy, M. V. Ramana

doi:10.1080/00304949209356691

Cited by 14 publications

(2 citation statements)

References 6 publications

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“…In most reports, dibenzylideneacetone, or derivatives thereof, were treated with symmetrical 1,3‐dicarbonyl compounds, such as cyclohexa‐1,3‐dione or malonic acid derivatives, as twofold Michael donors. Only a few examples that employ either chiral enolates as Michael donors16d,h or nonsymmetrical dialkenyl ketones16c,g,i,j,l are known, but none that combines these two features. The required dialkenyl ketone 11 was readily obtained by oxidation with MnO 2 of the respective alcohol, which in turn was prepared by 1,2‐addition of vinylmagnesium bromide to the aldol condensation product of propionaldehyde.…”

Section: Resultsmentioning

confidence: 99%

Spirodionic Acid, a Novel Metabolite from Streptomyces sp., Part 2: Total Synthesis through a Twofold Michael Addition as a Selective Spiroannelation Strategy

Siewert¹,

Textor²,

Grond³

et al. 2007

Chemistry A European J

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To elucidate the structure of the new natural product spirodionic acid, which has three stereogenic centers of hitherto unknown configuration, two 4-ethenylspiro[4.5]dec-6-en-1,8-diones with opposite relative configuration at C4 and C5 were prepared. The first access involved the synthesis of 3-ethenyl-2-formylcyclopentanone (8) using a three-component coupling process. A sequence of Michael addition to penten-3-one (7) and intramolecular aldol condensation then led to the highly selective formation of the 4S*,5S*-configured spirocycle 5. In contrast, a selective spiroannelation of a cyclohexenone ring was accomplished by a novel type of twofold Michael addition to the dialkenyl ketone 11 with subsequent dehydrogenation to furnish the 4S*,5R*-configured spirocycle 25. Diastereoselective methylation and oxidative degradation then completed a highly efficient synthesis of the natural product as prerequisite for the assignment of its absolute configuration.

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Section: Resultsmentioning

confidence: 99%

Spirodionic Acid, a Novel Metabolite from Streptomyces sp., Part 2: Total Synthesis through a Twofold Michael Addition as a Selective Spiroannelation Strategy

Siewert¹,

Textor²,

Grond³

et al. 2007

Chemistry A European J

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“…The Michael reaction of 1,5-diaryl-1,4-pentadien-3-ones with active methylene compounds have been the subject of many investigations [1][2][3][4][5][6]. It is known that a weak base or acid such as piperidine [7] or phosphorus trichloride [8] often afforded open chain adducts, while cyclic products have been obtained in presence of sodium methoxide [2] or sodium hydroxide [9].…”

Section: Introductionmentioning

confidence: 98%

Synthesis of 1,1-disubstituted-2,6-diarylcyclohexane-4-ones catalyzed by KF/basic Al2O3 under ultrasound

Li¹,

Xu²,

Chen³

et al. 2005

Ultrasonics Sonochemistry

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5,7-Diarylspiro[4,5,6,7-tetrahydrobenzo[d][1,2,3]selena/thiadiazole-6,5?-(hexahydropyrimidine)]-2?,4?,6?-triones/-2?-thioxo-4?,6?-diones from cyclohexanonedicarboxylates: Part V

Reddy¹,

Reddy²,

Padmavathi³

1999

Heteroatom Chem.

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The keto and gem‐ester functionalities of cyclohexanonedicarboxylates (1) offer a facile route for the synthesis of 5,7‐diarylspiro[4,5,6,7‐tetrahydrobenzo[d][1,2,3]selena/thiadiazole‐6,5′‐(hexahydropyrimidine)]‐2′,4′,6′‐triones (6 and 8) and ‐2′‐thioxo‐4′,6′‐diones (7 and 9). The new compounds were characterized by IR, NMR, and CMR spectral data. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 17–23, 1999

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Synthesis of Some Spiro-Isoxazolidine-3,5-Diones

Cited by 14 publications

References 6 publications

Spirodionic Acid, a Novel Metabolite from Streptomyces sp., Part 2: Total Synthesis through a Twofold Michael Addition as a Selective Spiroannelation Strategy

Spirodionic Acid, a Novel Metabolite from Streptomyces sp., Part 2: Total Synthesis through a Twofold Michael Addition as a Selective Spiroannelation Strategy

Synthesis of 1,1-disubstituted-2,6-diarylcyclohexane-4-ones catalyzed by KF/basic Al2O3 under ultrasound

5,7-Diarylspiro[4,5,6,7-tetrahydrobenzo[d][1,2,3]selena/thiadiazole-6,5?-(hexahydropyrimidine)]-2?,4?,6?-triones/-2?-thioxo-4?,6?-diones from cyclohexanonedicarboxylates: Part V

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