Diethyl 2-Oxopent-3-ynedioate: Synthesis and First Cyclizations of a Novel, Reactive Alkyne

Blitzke, Torsten; Sicker, Dieter; Wilde, H.

doi:10.1055/s-1995-3898

Cited by 20 publications

(5 citation statements)

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“…Ynone 7 also participated in cycloaddition reactions. A Diels–Alder reaction between 7 and 1,3-diphenylisobenzofuran generated polycyclic product 10 . Substituted phenol 11 was synthesized by treatment 7 with Danishefsky’s diene under thermal conditions …”

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confidence: 99%

A General Synthesis of Ynones from Aldehydes via Oxidative C–C bond Cleavage under Aerobic Conditions

2014

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confidence: 99%

A General Synthesis of Ynones from Aldehydes via Oxidative C–C bond Cleavage under Aerobic Conditions

2014

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“…in a comparable reaction conducted under thermal conditions . Rather than trying to stop the reaction after the first cycloaddition by changing the solvent or using a different dienophile, we chose to explore the alternative route described below.…”

Section: Resultsmentioning

confidence: 99%

Diastereoselective Syntheses of New Analogues of the Farnesyltransferase Inhibitor RPR 130401

et al. 2004

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The access to several benzo[f]perhydroisoindolic analogues of farnesyltransferase inhibitors from a single dienic precursor is reported. An initial [4 + 2] cycloaddition between diphenylisobenzofuran6 and pyrrolines 11, 14, and 15 led to either the syn or the anti isomers, depending on the mode of activation of the cycloaddition. The syn diastereomers were isolated in 90% de under 12 kbar at room temperature, while their anti counterparts were obtained with the same selectivity by warming the reaction mixture to 110 degrees C in toluene at atmospheric pressure. Both syn and anti adducts were separately N-deprotected, and the resulting amines reacted with an activated ester derived from the acid (20) to afford the final targets (5). Two new analogues (5a and 5b) of the FT inhibitor RPR 130401 were thus synthesized in a mere three-step synthetic scheme with overall yields from 30 to 60%.

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“…This elegant synthetic procedure has been successfully developed with phosphorane precursors 10 containing at least one electron-withdrawing group R 1 [R 1 = aryl, 7,8,[12][13][14][15][16][17] CO 2 R, [8][9][10][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] COSMe, 36 CN, [37][38][39][40][41][42][43][44][45] CHO, 46 COR, 20,47,48 SR, 49,50 SeR, 51,52 P(O)(OPh) 2…”

Section: Methodsmentioning

confidence: 99%

The Usefulness of Phosphorus Compounds in Alkyne Synthesis

2000

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Diethyl 2-Oxopent-3-ynedioate: Synthesis and First Cyclizations of a Novel, Reactive Alkyne

Cited by 20 publications

References 0 publications

A General Synthesis of Ynones from Aldehydes via Oxidative C–C bond Cleavage under Aerobic Conditions

A General Synthesis of Ynones from Aldehydes via Oxidative C–C bond Cleavage under Aerobic Conditions

Diastereoselective Syntheses of New Analogues of the Farnesyltransferase Inhibitor RPR 130401

The Usefulness of Phosphorus Compounds in Alkyne Synthesis

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